6-Amino-1,3-dihydro-2H-indol-2-one → HCID 25253371, compound

HRID 914073Notes

Reaction equation

HRID 914073 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=O)=[CH:24][C:23]=4OC)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1N=CC2[N:38](C)[C:39](=[O:52])C(F)(F)CN(C3CCCC3)C=2N=1.NC1C=C2C(CC(=O)N2)=CC=1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[C:29]5[C:25]([CH2:26][C:39](=[O:52])[NH:38]5)=[CH:24][CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 5905386-Amino-1,3-dihydro-2H-indol-2-oneHCID 252529054-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acidHCID 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 25253371HCID 25253371, compound

Procedure

The title compound was synthesized using an analogous procedure to that described in connection with 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid 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 6-aminoindolin-2-one. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45-1.86 (m, 6H) 1.92-2.16 (m, 2H) 3.39 (s, 3H) 3.54 (s, 2H) 3.87 (t, J=13.39 Hz, 2H) 4.74 (quin, J=8.27 Hz, 1H) 6.81 (d, J=8.34 Hz, 1H) 7.00 (br. s., 1H) 7.26 (s, 1H) 7.50 (br. s., 1H) 7.58 (s, 1H) 7.97 (s, 1H). [M+H] calc'd for C21H22F2N6O2, 429. found 429.

Sources & evidence

ORD record
ord-49adb44f51204e55983ec7c9e822ab77
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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