1,1'-Carbonyldiimidazole → HCID 71281084, compound

HRID 405857Notes

Reaction equation

[N:1]1[CH:2]=[C:3]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=O)=[O:11])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:36]=[C:37]([N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)[NH2:38]>CN1C(=O)CCC1>[CH3:22][C:21]1[CH:20]=[CH:19][C:15]([C:16]2[O:18][N:38]=[C:37]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[N:36]=2)=[CH:14][C:13]=1[NH:12][C:10]([C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1)=[O:11]

Participants

Conditions

Temperature: 105 °C

Procedure

A stirring suspension of 3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoic acid (4) (41 mg, 0.138 mmol) in anhydrous NMP (1 mL) was heated in the microwave at 105° C. for 2 minutes to dissolve all solid. Then, 1,1′-carbonyldiimidazole (22 mg, 0.138 mmol) was added and the reaction was stirred at room temperature for 15 minutes. N′-hydroxymorpholine-4-carboximidamide (20 mg, 0.138 mmol) was added and the reaction was stirred for 30 minutes. The reaction was heated in the microwave at 130° C. for 15 minutes. The crude product was purified by reverse phase preparative HPLC to give N-(2-methyl-5-(3-morpholino-1,2,4-oxadiazol-5-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (F75). 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.52-9.48 (m, 1H), 8.68 (s, 1H), 8.11 (d, J=2.0 Hz, 1H), 7.88-7.83 (m, 2H), 7.68-7.63 (m, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.31-7.27 (m, 1H), 3.72-3.69 (m, 4H), 3.41-3.38 (m, 4H), 2.39 (s, 3H). MS m/z 405.16 (M+1)+.

Workup

dissolutionto dissolve all solid
stirringthe reaction was stirred for 30 minutes
temperatureThe reaction was heated in the microwave at 130° C. for 15 minutes
customThe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-6bbd3ad6c64749f28b603bf6126ff957
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754071B2

Reaction notes

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