Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 60207433, compound

HRID 1192211Notes

Reaction equation

HRID 1192211 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:19])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[C:17]#[N:18].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:44][N:45]([CH3:59])[CH2:46][CH2:47][CH2:48][O:49][C:50]1[CH:56]=[CH:55][C:53]([NH2:54])=[CH:52][C:51]=1[O:57][CH3:58]>>[C:17]([C:10]1[CH:11]=[C:12]([C:14]([NH:54][C:53]2[CH:55]=[CH:56][C:50]([O:49][CH2:48][CH2:47][CH2:46][N:45]([CH3:59])[CH3:44])=[C:51]([O:57][CH3:58])[CH:52]=2)=[O:16])[S:13][C:9]=1[S:8][C:7]1[C:6]([Cl:19])=[CH:5][N:4]=[CH:3][C:2]=1[Cl:1])#[N:18]

Participants

4

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60207415HCID 60207415, compoundHCID 60207419HCID 60207419, compound

Product 1

HCID 60207433HCID 60207433, compound

Procedure

Prepared according to the procedure described for example 70 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-cyano-thiophene-2-carboxylic acid (100 mg, 0.3 mmol) from step C of example 203, 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (126 mg, 0.33 mmol) and 4-(3-dimethylaminopropoxy)-3-methoxy-aniline (96 mg, 0.36 mmol) from the above. The crude material was purified by reverse phase HPLC and the title compound was obtained as a yellow solid (15.0 mg, 9% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.33 (1H, s), 8.85 (2H, s), 8.24 (1H, s), 7.29 (1H, m), 7.18 (1H, m), 6.94 (1H, m), 3.94 (2H, m), 2.34 (2H, m), 2.14 (6H, s), 1.84 (3H, s), 1.81 (2H, m). MS m/z: 537.17, 539.15 [M+H]+.

Workup

  1. customPrepared
  2. customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4bbf1a23b03748fe88ccdb6c706fe221
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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