Thionyl Chloride → HCID 89534606, compound

HRID 2176039Notes

Reaction equation

O[CH2:2][CH2:3][N:4]([CH2:10][C:11]1[CH:12]=[C:13]([CH:47]=[CH:48][CH:49]=1)[C:14]([NH:16][C:17]1[S:18][C:19]2[CH2:46][CH2:45][CH2:44][CH2:43][C:20]=2[C:21]=1[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)=[CH:27][CH:26]=1)=[O:23])=[O:15])[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7].S(Cl)(Cl)=O.[NH:54]1[CH2:64][CH2:63][CH:57]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH2:56][CH2:55]1>>[CH3:40][O:39][C:37]([C:36]1[CH:41]=[CH:42][C:33]([CH2:32][CH2:31][C:28]2[CH:27]=[CH:26][C:25]([NH:24][C:22]([C:21]3[C:20]4[CH2:43][CH2:44][CH2:45][CH2:46][C:19]=4[S:18][C:17]=3[NH:16][C:14]([C:13]3[CH:12]=[C:11]([CH:49]=[CH:48][CH:47]=3)[CH2:10][N:4]([CH:5]([CH2:6][CH3:7])[CH2:8][CH3:9])[CH2:3][CH2:2][N:54]3[CH2:55][CH2:56][CH:57]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH2:63][CH2:64]3)=[O:15])=[O:23])=[CH:30][CH:29]=2)=[CH:34][CH:35]=1)=[O:38]

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 70770Ethyl 4-piperidinecarboxylate

HCID 90370292HCID 90370292, compound

Product 1

HCID 89534606HCID 89534606, compoundYield 86.8%

Procedure

By a method similar to Preparation Example 37, 197 mg of methyl 4-(2-{4-[({2-[(3-{[(2-hydroxyethyl)(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate was reacted with 0.10 mL of thionyl chloride, and then the resultant was reacted with 325 mg of ethyl isonipecotate, thereby obtaining 206 mg of ethyl 1-(2-{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)benzyl](pentan-3-yl)amino}ethyl)piperidine-4-carboxylate.

Sources & evidence

ORD record: ord-b592b7ff1dc34fe3b3dec63959c63222
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062032B2

Reaction notes

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