4-methyl-1H-indol-5-amine → HCID 66778958, compound

HRID 1470376Notes

Reaction equation

HRID 1470376 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=3)[O:10][C:3]=12.[CH3:19][C:20]1[C:28]([NH2:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2>>[CH3:19][C:20]1[C:28]([NH:29][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=4)[O:10][C:3]=23)=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66779647HCID 66779647, compound

Product 1

HCID 66778958HCID 66778958, compound

Procedure

The title compound was prepared by procedure E using [4-(7-chlorofuro[3,2-b]pyridin-2-yl)phenyl]methanol (20.40 mg; 0.08 mmol; 1.00 eq.) instead of 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine, and 4-methyl-1H-indol-5-ylamine (12.06 mg; 0.08 mmol; 1.05 eq.) instead of 6-amino-2,2-difluoro-4H-benzo[1,4]oxazin-3-one, and was obtained as a beige solid (8 mg, 28%). (HPLC (method F): 97%, RT: 3.30 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.14 (s, 1H), 8.54 (s, 1H), 7.94 (d, J=5.4, 1H), 7.91 (d, J=8.2, 2H), 7.42 (d, J=8.1, 2H), 7.40-7.35 (m, 2H), 7.30 (d, J=8.3, 1H), 7.00 (d, J=8.4, 1H), 6.52 (s, 1H), 6.09 (d, J=5.4, 1H), 5.26 (s, 1H), 4.55 (d, J=5.6, 2H), 2.36 (s, 3H); MS (m/z) 370 [M+H]+, RT: 3.2 min.

Sources & evidence

ORD record
ord-7d080c3efe854a38b428791c2efe8427
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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