4-methyl-1H-indol-5-amine → HCID 56848875, compound

HRID 1470377Notes

Reaction equation

HRID 1470377 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]([C:17](O)([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[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>>[C: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:31][C:30]3[C:22]([CH3:21])=[C:23]4[C:27](=[CH:28][CH:29]=3)[NH:26][CH:25]=[CH:24]4)[CH:8]=2)=[CH:12][CH:13]=1)([CH3:19])=[CH2:18]

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66779658HCID 66779658, compound

Product 1

HCID 56848875HCID 56848875, compound

Procedure

The title compound was prepared by procedure E using 2-[4-(7-chlorofuro[3,2-b]pyridin-2-yl)phenyl]propan-2-ol (29.50 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 (15.74 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 (26 mg, 66%). (HPLC (method F): 93%, RT: 4.44 min); 1H NMR (500 MHz, DMSO-d6) δ[ppm] 11.14 (s, 1H), 8.57 (s, 1H), 7.99-7.90 (m, 3H), 7.62 (d, J=8.5, 2H), 7.44 (s, 1H), 7.38 (t, J=2.7, 1H), 7.31 (d, J=8.4, 1H), 7.01 (d, J=8.4, 1H), 6.52 (s, 1H), 6.09 (d, J=5.5, 1H), 5.55 (s, 1H), 5.18 (s, 1H), 2.36 (s, 3H), 2.16 (s, 3H); MS (m/z) 380 [M+H]+, RT: 4.4 min.

Sources & evidence

ORD record
ord-4df7320c383b41a0b9a08cb35b29430a
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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