5-Aminoindole → HCID 25253372, compound

HRID 914074Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]([F:19])([F:18])[CH2:9][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[CH:26]2>>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([NH:22][C:2]3[N:3]=[CH:4][C:5]4[N:6]([CH3:21])[C:7](=[O:20])[C:8]([F:19])([F:18])[CH2:9][N:10]([CH:13]5[CH2:17][CH2:16][CH2:15][CH2:14]5)[C:11]=4[N:12]=3)=[CH:31][CH:30]=2)[CH:26]=[CH:27]1

Participants

Reactant 2

HCID 788675-Aminoindole

HCID 579555742-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[4,5-B][1,4]diazepin-6(7H)-one

Product 1

HCID 25253372HCID 25253372, compound

Procedure

The title compound was prepared using Buchwald reaction from 2-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[5,4-b][1,4]diazepin-6(7H)-one and 5-aminoindole. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (m, 4H) 1.69 (m, 2H) 1.97 (m, 2H) 3.3 (s, 3H) 3.99 (t, J=14.3 Hz, 2H) 4.75 (t, J=8.0 Hz, 1H) 6.29 (br. s., 1H) 7.18-7.41 (m, 3H) 7.96 (s, 1H) 8.18 (s, 1H) 9.16 (s, 1H) 10.91 (br. s., 1H). [M+H] calc'd for C21H22F2N6O, 413. found 413.

Sources & evidence

ORD record: ord-93c64b107d464438acbe1d17089259a8
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026234B2

Reaction notes

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