Citric Acid → HCID 86634200, compound

HRID 644186Notes

Reaction equation

HRID 644186 reaction equation
C(O)(=O)[CH2:2][C:3]([CH2:8]C(O)=O)([C:5](O)=O)[OH:4].[C:14]([O:18][C:19]([NH:21][CH:22]1[CH2:26][CH2:25][N:24]([C:27]2[CH:51]=[CH:50][C:30]([C:31]([NH:33][C:34]3[CH:49]=[CH:48][CH:47]=[CH:46][C:35]=3[C:36]([NH:38][C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=3)=[O:37])=[O:32])=[C:29]([O:52][CH:53]3[CH2:58][CH2:57][N:56](C(OC(C)(C)C)=O)[CH2:55][CH2:54]3)[CH:28]=2)[CH2:23]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].FC1C=CC([C:71](NC2C=CC=CC=2C(NC2C=CC(Cl)=CN=2)=O)=[O:72])=C(OC2CCN(C(OC(C)(C)C)=O)CC2)C=1.C(OC(NC1CCNC1)=O)(C)(C)C>>[C:14]([O:18][C:19]([NH:21][CH:22]1[CH2:26][CH2:25][N:24]([C:27]2[CH:51]=[CH:50][C:30]([C:31]([NH:33][C:34]3[CH:49]=[CH:48][CH:47]=[CH:46][C:35]=3[C:36]([NH:38][C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=3)=[O:37])=[O:32])=[C:29]([O:52][CH:53]3[CH2:54][CH2:55][N:56]([O:4][C:3]([CH3:8])([CH3:5])[CH3:2])[C:57](=[C:71]=[O:72])[CH2:58]3)[CH:28]=2)[CH2:23]1)=[O:20])([CH3:16])([CH3:17])[CH3:15]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 685302072-[4-Fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamideHCID 68532436HCID 68532436, compound

Product 1

HCID 86634200HCID 86634200, compound

Procedure

Using methods substantially equivalent to those described in Example 4-F except that saturated aqueous citric acid was used instead of water in the workup, 2-[4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (234 mg, 0.32 mmol, 44%) was prepared from 2-[4-fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide and 3-tert-butoxycarbonylaminopyrrolidine.

Sources & evidence

ORD record
ord-07b69f044764476c93665ddb8ea4c80d
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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