Carbamate → 1-(4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)-3-(4-(piperazin-1-yl)phenyl)urea

HRID 75438Notes

Reaction equation

HRID 75438 reaction equation
NC(N)=O.C(=O)([O-])N.C12OC(CC1)CN(C1C=C(CS(C)(=O)=O)N=C(C3C=CC(N)=CC=3)N=1)C2.[CH:35]12[O:42][CH:39]([CH2:40][CH2:41]1)[CH2:38][N:37]([C:43]1[CH:48]=[C:47]([CH2:49][S:50]([CH3:53])(=[O:52])=[O:51])[N:46]=[C:45]([C:54]3[CH:59]=[CH:58][C:57]([NH:60][C:61](=[O:82])[NH:62][C:63]4[CH:68]=[CH:67][C:66]([N:69]5[CH2:74][CH2:73][N:72](C(OC(C)(C)C)=O)[CH2:71][CH2:70]5)=[CH:65][CH:64]=4)=[CH:56][CH:55]=3)[N:44]=1)[CH2:36]2.FC(F)(F)C(O)=O>ClCCl>[CH:39]12[O:42][CH:35]([CH2:41][CH2:40]1)[CH2:36][N:37]([C:43]1[CH:48]=[C:47]([CH2:49][S:50]([CH3:53])(=[O:51])=[O:52])[N:46]=[C:45]([C:54]3[CH:59]=[CH:58][C:57]([NH:60][C:61]([NH:62][C:63]4[CH:68]=[CH:67][C:66]([N:69]5[CH2:70][CH2:71][NH:72][CH2:73][CH2:74]5)=[CH:65][CH:64]=4)=[O:82])=[CH:56][CH:55]=3)[N:44]=1)[CH2:38]2

Participants

7

Reactant 5

HCID 276CarbamateHCID 1176UreaHCID 6422Trifluoroacetic acidHCID 66750277HCID 66750277, compoundHCID 67607491HCID 67607491, compound

Product 1

HCID 497643851-(4-(4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)-3-(4-(piperazin-1-yl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)phenyl)piperazine-1-carboxylate was obtained according to the general procedure for formation of urea or carbamate compounds from 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)aniline (44). Removal of the Boc group in tert-butyl 4-(4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)phenyl)piperazine-1-carboxylate (85.2 mg, 0.126 mmoles) by treatment with trifluoroacetic acid in dichloromethane gave the title compound. Yield: 70.0 mg (38% over 2 steps). RT 1.64, M+H=578.2.

Sources & evidence

ORD record
ord-edc050be6d4743f0b065629e67417aa7
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

Loading…