4-methyl-1H-indol-5-amine → HCID 56848873, compound

HRID 1470369Notes

Reaction equation

HRID 1470369 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]([O:17][CH3:18])=[C:13]([CH3:19])[CH:12]=3)[O:10][C:3]=12.[CH3:20][C:21]1[C:29]([NH2:30])=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[CH:24][NH:25]2>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[NH:30][C:29]3[C:21]([CH3:20])=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)[CH:8]=2)=[CH:12][C:13]=1[CH3:19]

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66778966HCID 66778966, compound

Product 1

HCID 56848873HCID 56848873, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(4-methoxy-3-methylphenyl)furo[3,2-b]pyridine (29.40 mg; 0.11 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 (16.49 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 (30 mg, 73%). (HPLC (method F): 97%, RT: 4.34 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.14 (s, 1H), 8.49 (s, 1H), 7.92 (d, J=5.5, 1H), 7.77 (d, J=8.6, 1H), 7.66 (s, 1H), 7.38 (s, 1H), 7.30 (d, J=8.4, 1H), 7.22 (s, 1H), 7.02 (dd, J=17.9, 8.5, 2H), 6.52 (s, 1H), 6.09 (d, J=5.5, 1H), 3.85 (s, 3H), 2.36 (s, 3H), 2.18 (s, 3H); MS (m/z) 384 [M+H]+, RT: 4.2 min.

Sources & evidence

ORD record
ord-af4bf1e901ba49c78fff31adf99bacf2
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

Loading…