HCID 57955658, compound → HCID 57955565, compound

HRID 1880959Notes

Reaction equation

[CH:1]1([N:6]2[CH2:12][C@:11]([F:15])([CH:13]=[CH2:14])[C:10](=[O:16])[N:9]([CH3:17])[C:8]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[C:32]([O:33][CH3:34])=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([F:35])[CH:24]=4)=[N:21][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[CH:1]1([N:6]2[CH2:12][C@:11]([F:15])([CH:13]=[CH2:14])[C:10](=[O:16])[N:9]([CH3:17])[C:8]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[C:32]([O:33][CH3:34])=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([F:35])[CH:24]=4)=[N:21][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of (R)-methyl 4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoate (400 mg, 0.821 mmol) was suspended in conc. HCl (1.0 mL) and it was stirred at 95° C. for 3-4 hrs. At this time the reaction was cooled to room temperature and filtered to reveal the product as a tan solid (295 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48-1.82 (m, 4 H) 1.98-2.02 (m, 4 H) 3.29 (s, 3 H) 3.51 (br. s., 2 H) 3.94 (s, 3 H) 4.88 (t, J=8.08 Hz, 1 H) 5.30-5.47 (m, 2 H) 6.01 (ddd, J=17.43, 12.63, 10.86 Hz, 1 H) 7.41-7.57 (m, 1 H) 7.82 (s, 1 H) 8.12 (s, 1 H) 8.31 (d, J=8.08 Hz, 1 H). [M+H] calc'd for C23H25F2N5O4, 474; found 474.

Workup

temperatureAt this time the reaction was cooled to room temperature
filtrationfiltered

Sources & evidence

ORD record: ord-b7308cc66a8f43ea95a18905e6870764
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318727B2

Reaction notes

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