4-methyl-1H-indol-5-amine → HCID 66779695, compound

HRID 1470370Notes

Reaction equation

HRID 1470370 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]([CH3:17])[CH:12]=3)[O:10][C:3]=12.[CH3:18][C:19]1[C:27]([NH2:28])=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2>>[CH3:18][C:19]1[C:27]([NH:28][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=4)[O:10][C:3]=23)=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66779659HCID 66779659, compound

Product 1

HCID 66779695HCID 66779695, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(3-methylphenyl)furo[3,2-b]pyridine (23.00 mg; 0.09 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 (14.49 mg; 0.10 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 (22 mg, 67%). (HPLC (method F): 99%, RT: 4.24 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.15 (s, 1H), 8.55 (s, 1H), 7.96 (d, J=5.5, 1H), 7.75 (d, J=7.5, 1H), 7.69 (s, 1H), 7.44-7.34 (m, 3H), 7.31 (d, J=8.3, 1H), 7.22 (d, J=7.3, 1H), 7.01 (d, J=8.4, 1H), 6.52 (s, 1H), 6.13 (d, J=5.5, 1H), 2.36 (s, 3H), 2.35 (s, 3H); MS (m/z) 354 [M+H]+, RT: 4.1 min.

Sources & evidence

ORD record
ord-8441af0bdb6849fd9523d7861f15d641
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

Loading…