Ammonia → HCID 178466592, compound

HRID 1713734Notes

Reaction equation

N.[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[O:16][C:15]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C@H:26]4[CH2:31][CH2:30][C@H:29]([CH2:32][C:33]([OH:35])=O)[CH2:28][CH2:27]4)=[CH:22][CH:21]=3)=[O:18])=[N:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:3].CC[N:38]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>O.CN(C=O)C>[NH2:38][C:33](=[O:35])[CH2:32][C@H:29]1[CH2:28][CH2:27][C@H:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:17]([C:15]3[O:16][C:12]([NH:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:2][CH3:3])[CH:6]=4)=[N:13][N:14]=3)=[O:18])=[CH:21][CH:22]=2)[CH2:31][CH2:30]1

Participants

Conditions

Temperature: 100 °C

Procedure

Ammonia (0.06 mL of a 28-30% wt % solution in water) was added to a stirred mixture of (trans-4-{4-[({5-[(3-ethoxyphenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetic acid (Example 113, 65 mg), EDAC (32 mg), and HOBt (23 mg) in DMF (1 mL). The mixture was stirred for 16 h then was diluted with DMF (2 mL) and heated to 100° C. for 30 minutes in an Emrys Optimizer™ microwave. The crude mixture was purified directly by HPLC using a gradient of 25-75% acetonitrile/water with 1% ammonia as the eluent to give the title compound (10 mg) as a solid; 1H NMR δ 10.82 (2H, bs), 7.68 (2H, d), 7.22 (5H, m), 7.08 (1H, 1H), 6.67 (1H, s), 6.56 (1H, m), 4.00 (2H, quartet), 2.50 (1H+ DMSO, m), 1.96 (2H, d), 1.83-1.66 (5H, m), 1.42 (2H, m), 1.33(3H, t), 1.08 (2H, m); MS m/e MH+ 474.

Workup

customThe crude mixture was purified directly by HPLC

Sources & evidence

ORD record: ord-b23e559827304dd6a8eca6217bcd89cc
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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