2486-69-3 → 4-(9-Cyclopentyl-7-ethyl-7-fluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

HRID 914168Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH2:15][CH3:16])([F:14])[CH2:8][N:7]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:6]=2[N:22]=1.[NH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=1[O:33][CH3:34]>Cl.C(O)(C)C>[CH:17]1([N:7]2[CH2:8][C:9]([CH2:15][CH3:16])([F:14])[C:10](=[O:13])[N:11]([CH3:12])[C:5]3[CH:4]=[N:3][C:2]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=4[O:33][CH3:34])=[N:22][C:6]2=3)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-9-cyclopentyl-7-ethyl-7-fluoro-5-methyl-8,9-dihydro-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one (630 mg, 1.93 mmol), 4-amino-3-methoxybenzoic acid (484 mg, 2.9 mmol), isopropanol (20 ml), and concentrated hydrochloric acid (10 drops) was stirred at 100° C. for 20 h. Solid was filtered to give 730 mg product as white solid (83%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.3 Hz, 3H) 1.56 (br. s., 3H) 1.67-1.96 (m, 6H) 3.28 (s, 3H) 3.74-3.92 (m, 3H) 3.94 (s, 3H) 4.91 (t, J=7.8 Hz, 1H) 7.21-7.43 (m, 1H) 7.47-7.69 (m, 2H) 8.13 (d, J=8.1 Hz, 1H) 8.24 (s, 1H) 9.32 (br. s., 1H). [M+H] calc'd for C23H28FN5O4, 458. found 458.

Workup

filtrationSolid was filtered

Sources & evidence

ORD record: ord-203abeec1fe949e785fac0640ecd2acf
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026234B2

Reaction notes

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