Ammonia → HCID 15292748, compound

HRID 2210600Notes

Reaction equation

HRID 2210600 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[NH:19][CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28].CN(C)[C:38](Cl)=[O:39].N>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([O:39][CH2:38][C:20]6[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=6)=[CH:23][CH:24]=5)[N:19]([C:27]([O:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[O:28])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6598Dimethylcarbamoyl ChlorideHCID 15891Phenyl chloroformateHCID 9928151HCID 9928151, compound

Product 1

HCID 15292748HCID 15292748, compound

Procedure

The desired compound was prepared according to the method of Example 2, except substituting 3-(pyridin-3-yl)-7-(6-phenylmethoxyindol-3-)carbonyl-1H,3H-pyrrolo[1,2-c]thiazole, prepared as in Example 4 for 3-(pyridin-3-yl)-7-(indol-3-yl)carbonyl-1H,3H-pyrrolo[1,2-c]thiazole and substituting phenyl chloroformate for N,N-dimethylcarbamoyl chloride. 1H NMR (DMSO-d6, 300 MHz) δ4.45 (d, 1H, J=15 Hz), 4.62 (dd, 1H, J=15 Hz, 2 Hz), 5.16 (s, 2H), 6.69 (d, 1H, J=3 Hz), 6.76 (s, 1H), 6.85 (d, 1H, J=3 Hz), 7.12 (dd, 1H, J=9 Hz, 3 Hz), 7.26-7.52 (m, 11H), 7.60-7.68 (m, 1H), 7.77 (d, 1H, J=3 Hz), 8.08 (d, 1H, J=9 Hz), 8.30 (s, 1H), 8.51-8.54 (m, 2H), MS (DCI/NH3) m/e 572 (M+H)+.

Sources & evidence

ORD record
ord-4e110efb603843508c9a3899c9e6d591
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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