Dimethylamine → HCID 57731441, compound

HRID 2234702Notes

Reaction equation

HRID 2234702 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:21]=[CH:22][CH:23]=[C:24]5[C:28]=4[NH:27][CH:26]=[CH:25]5)=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:29][NH:30][CH3:31].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:21]=[CH:22][CH:23]=[C:24]5[C:28]=4[NH:27][CH:26]=[CH:25]5)=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([N:30]([CH3:31])[CH3:29])=[O:5]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57731620HCID 57731620, compound

Product 1

HCID 57731441HCID 57731441, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-amino-5-[3-(1H-indol-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid (70 mg, 0.11 mmol), dimethylamine (2 N solution in THF, 0.11 mL, 0.22 mmol), diisopropylethylamine (20 mg, 0.16 mmol) in DMF (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (60 mg, 0.16 mmol). The resulting solution was stirred at room temperature for 1 hour. The mixture was diluted with DMF (1 mL) and directly used in purification by mass-triggered reverse-phase HPLC to afford 2-amino-5-[3-(1H-indol-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a white solid (3 mg, 7%). MS: m/z 396 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.90 (s, 6H), 5.21 (s, 2H), 6.49 (d, 1H), 6.79 (d, 1H), 7.10 (t, 1H), 7.30 (d, 2H), 7.33 (d, 1H), 7.43 (dd, 1H), 7.49 (d, 1H), 7.81 (d, 1H), 8.03 (d, 1H), 8.44 (m, 2H), 10.89 (s, 1H), 11.99 (s, 1H).

Workup

  1. customdirectly used in purification by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-d8870a70446e4844a14b2f4dee0d4db3
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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