Cyclopropanecarbonyl chloride → 3-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-4-methoxyphenyl]benzamide

HRID 2190413Notes

Reaction equation

HRID 2190413 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=4)[CH:15]=[CH:16][C:17]=3[O:18][CH3:19])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:37]([CH:34]4[CH2:36][CH2:35]4)=[O:38])[S:3][C:4]=3[CH:10]=2)[CH:13]=1)=[O:33])([CH3:30])[CH3:29])#[N:32]

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86655369HCID 86655369, compound

Product 1

HCID 866553703-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-4-methoxyphenyl]benzamideYield 45%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methoxyphenyl}-3-(1-cyano-1-methylethyl)benzamide (115 mg, 0.25 mmol), cyclopropanecarbonyl chloride (105 mg, 1.00 mmol), N,N-dimethylpyridine-4-amine (122 mg, 1.00 mmol) and pyridine (2 mL), and in the same manner as in Example A18(v), the title compound (59 mg, 45%) was obtained as a pale-yellow powder.

Sources & evidence

ORD record
ord-39631d4eff704a909749b65a8b9fc9d7
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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