(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 59317994, compound

HRID 2190641Notes

Reaction equation

HRID 2190641 reaction equation
ClC1C=CC(C(NC2C=CC(C)=C(I)C=2)=O)=CN=1.C(N[C@@H]1CCNC1)(OC(C)(C)C)=O.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][C:48]([C:51](=[O:61])[NH:52][C:53]3[CH:58]=[CH:57][C:56]([CH3:59])=[C:55]([I:60])[CH:54]=3)=[CH:47][N:46]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]>>[C:32]([O:36][C:37](=[O:38])[NH:39][C@@H:40]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][C:48]([C:51](=[O:61])[NH:52][C:53]3[CH:58]=[CH:57][C:56]([CH3:59])=[C:55]([I:60])[CH:54]=3)=[CH:47][N:46]=2)[CH2:41]1)([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 3

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 79255626-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamideHCID 593181844-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59317994HCID 59317994, compound

Procedure

{(R)-1-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester was prepared from 6-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamide and (+)-(R)-3-(Boc-amino)pyrrolidine following a method similar to the one described in the synthesis of 4-[5-(3-iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester above. The product was isolated after a silica gel column purification and a precipitation out of THF with excess of hexanes. HRMS m/z calcd for C22H27N4O3I [M+H]+: 523.1201. Found: 523.1201.

Workup

  1. customThe product was isolated
  2. customafter a silica gel column purification
  3. customa precipitation out of THF with excess of hexanes

Sources & evidence

ORD record
ord-2b25464ad15b4a0cae4b90d619265a28
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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