Cyclopentylamine → HCID 44419222, compound

HRID 1364559Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of Example 181F (36.5 mg, 0.1 mmol) and cyclopentylamine (25.5 mg, 0.3 mmol) in N,N-dimethylacetamide (1.5 ml) was stirred in a sealed tube. This reaction mixture was heated in a microwave reactor at 160° C. for 20 min. and purified on HPLC (10 mM ammonium acetate, 5% acetonitirle in H2O/CH3CN) to give titled compound (33.5 mg, 81%). 1H NMR (300 MHz, DMSO-d6) δ 8.97 (t, J=6.0 Hz, 1H), 7.88 (d, J=9.0 Hz, 2H), 7.53 (d, J=9.0 Hz, 2H), 6.89 (s, 2H), and 6.70 (s, 1H), 6.27 (d, J=6.0 Hz, 2H), 4.57 (d, J=6.0 Hz, 2H), 4.57 (m, 1H), 3.18 (s, 3H), 1.95 (m, 1H), 1.67 (m, 2H), 1.50 (m, 4H); MS (APCI) m/z 414 [M+H]+, 412 [M−H]−.

Workup

custompurified on HPLC (10 mM ammonium acetate, 5% acetonitirle in H2O/CH3CN)

Sources & evidence

ORD record: ord-4bbab2c613c049198e5ec8a246cc5fb1
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888374B2

Reaction notes

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