4-methyl-1H-indol-5-amine → HCID 66779764, compound

HRID 1470368Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[C:13]([CH3:20])[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>>[CH3:19][O:18][C:14]1[C:15]([CH3:17])=[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][C:13]=1[CH3:20]

Participants

Reactant 2

HCID 154344964-methyl-1H-indol-5-amine

HCID 66779723HCID 66779723, compound

Product 1

HCID 66779764HCID 66779764, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(4-methoxy-3,5-dimethylphenyl)furo[3,2-b]pyridine (28.90 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 (15.42 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 white solid (22 mg, 56%). (HPLC (method F): 99%, RT: 4.37 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.15 (s, 1H), 8.51 (s, 1H), 7.94 (d, J=5.5, 1H), 7.54 (s, 2H), 7.38 (t, J=2.7, 1H), 7.30 (d, J=8.3, 1H), 7.25 (s, 1H), 7.00 (d, J=8.4, 1H), 6.52 (s, 1H), 6.14 (d, J=5.5, 1H), 3.69 (s, 3H), 2.35 (s, 3H), 2.25 (s, 6H); MS (m/z) 398 [M+H]+, RT: 4.2 min.

Sources & evidence

ORD record: ord-9655073d616e4ae28823e0b42547b325
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006440B2

Reaction notes

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