Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 118117019, compound

HRID 1774627Notes

Reaction equation

HRID 1774627 reaction equation
[CH3:1][C:2]1([CH3:46])[CH2:13][C:12]2[CH:11]=[C:10]3[N:5]([CH2:6][CH2:7][N:8]([C:15]4[C:20]([CH2:21][OH:22])=[C:19]([C:23]5[CH:24]=[C:25]([NH:31][C:32]6[CH:37]=[CH:36][N:35]=[C:34]([N:38]7[CH2:42][CH2:41][CH:40]([C:43](O)=[O:44])[CH2:39]7)[N:33]=6)[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=5)[CH:18]=[CH:17][N:16]=4)[C:9]3=[O:14])[C:4]=2[CH2:3]1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)O[N:58]1[C:62]2N=CC=C[C:61]=2[N:60]=N1>C(N(CC)CC)C.NCC#N.C1COCC1>[C:62]([CH2:61][NH:60][C:43]([CH:40]1[CH2:41][CH2:42][N:38]([C:34]2[N:33]=[C:32]([NH:31][C:25]3[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=[C:23]([C:19]4[CH:18]=[CH:17][N:16]=[C:15]([N:8]5[CH2:7][CH2:6][N:5]6[C:10](=[CH:11][C:12]7[CH2:13][C:2]([CH3:46])([CH3:1])[CH2:3][C:4]=76)[C:9]5=[O:14])[C:20]=4[CH2:21][OH:22])[CH:24]=3)[CH:37]=[CH:36][N:35]=2)[CH2:39]1)=[O:44])#[N:58]

Participants

6

Reactant 2

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118116299HCID 118116299, compound

Product 1

HCID 118117019HCID 118117019, compoundYield 28.3%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 10901AminoacetonitrileCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A 50 mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 102c (100 mg, 0.16 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (HATU, 152 mg, 0.40 mmol), triethylamine (TEA, 8 drops), THF (10 mL), and 2-aminoacetonitrile (5 drops). The mixture was heated at 30° C. for 5 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 102 (30 mg, 28%) as a white solid. MS: [M+H]+ 663.2. 1H NMR (500 MHz, DMSO-d6) δ 8.88 (d, J=6.0 Hz, 1H), 8.81 (s, 1H), 8.74 (s, 1H), 8.47 (d, J=5.0 Hz, 1H), 7.95 (d, J=5.5 Hz, 1H), 7.71 (s, 1H), 7.35 (d, J=4.5 Hz, 1H), 6.58-6.55 (m, 2H), 5.02 (s, 1H), 4.53-4.51 (m, 1H), 4.43-4.40 (m, 1H), 4.23-4.15 (m, overlap, 5H), 3.86-3.84 (m, 1H), 3.72-3.69 (m, 1H), 3.62 (s, 3H), 3.60-3.56 (m, 1H), 3.51-3.43 (m, 2H), 3.10-3.08 (m, 1H), 2.62-2.54 (m, 2H), 2.43 (s, 2H), 2.18-2.16 (m, 1H), 2.06-2.04 (m, 1H), 1.22 (s, 6H).

Workup

  1. customA 50 mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureAfter this time the reaction was cooled to room temperature
  3. filtrationIt was then filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-8b34925453744c7fa3c4fe5cf25747d0
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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