Pyrrolo[3,2-b]pyridin-1-ylamine → HCID 59200063, compound

HRID 2382023Notes

Reaction equation

N1(N)C2C(=NC=CC=2)C=[CH:2]1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([NH:22][C:23]([C:25]1[CH:26]=[N:27][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[N:29][CH:30]=1)=[O:24])[CH:17]=[CH:16]2>>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([NH:22][C:23]([C:25]1[C:26]([CH3:2])=[N:27][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[N:29][CH:30]=1)=[O:24])[CH:17]=[CH:16]2

Participants

Reactant 2

HCID 19601545Pyrrolo[3,2-b]pyridin-1-ylamine

HCID 86639376HCID 86639376, compound

Product 1

HCID 59200063HCID 59200063, compound

Conditions

Temperature: 150 °C

Procedure

Following procedures similar to those of Example 127, but substituting 5-methoxy-indol-1-ylamine for pyrrolo[3,2-b]pyridine-1-ylamine, and the reaction is stirred at 150° C. for 1 h, there is prepared 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methoxy-indol-1-yl)-amide (22%) as a solid. MS: 360 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.88 (s, 3H), 3.84 (s, 3H), 6.50 (d, H) 6.90 (m, H), 7.13 (d, H), 7.25-7.34 (m, 2H), 7.60 (m, H), 8.05 (m, H), 8.65 (d, H), 8.79 (d, H), 9.20 (s, 2H).

Sources & evidence

ORD record: ord-8fe86be1b238468583706d97394e49cd
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

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