4-methyl-1H-indol-5-amine → HCID 66779317, compound

HRID 1470374Notes

Reaction equation

HRID 1470374 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][CH:14]=[C:13]([O:17][CH3:18])[C:12]=3[O:19][CH3:20])[O:10][C:3]=12.[CH3:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2>>[CH3:20][O:19][C:12]1[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[O:10][C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[NH:31][C:30]2[C:22]([CH3:21])=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][CH:25]=[CH:24]3)[CH:8]=1

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66779595HCID 66779595, compound

Product 1

HCID 66779317HCID 66779317, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(2,3-dimethoxyphenyl)furo[3,2-b]pyridine (30.00 mg; 0.10 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 (15.89 mg; 0.11 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 (15 mg, 37%). (HPLC (method F): 99%, RT: 4.00 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.16 (s, 1H), 8.59 (s, 1H), 7.97 (d, J=5.5, 1H), 7.60 (d, J=7.6, 1H), 7.43-7.36 (m, 1H), 7.36-7.27 (m, 2H), 7.20-7.11 (m, 2H), 7.00 (d, J=8.5, 1H), 6.52 (s, 1H), 6.10 (d, J=5.5, 1H), 3.88 (s, 3H), 3.87 (s, 3H), 2.36 (s, 3H); MS (m/z) 400 [M+H]+, RT: 3.3 min.

Sources & evidence

ORD record
ord-551404f7505f4f5c9aba3689195f3a1b
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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