Dicyclohexylcarbodiimide → HCID 67434865, compound

HRID 1037692Notes

Reaction equation

HRID 1037692 reaction equation
C(OC([NH:8][CH2:9][C:10]([OH:12])=[O:11])=O)(C)(C)C.[CH:13]1([N:19]=[C:20]=NC2CCCCC2)CCCC[CH2:14]1.CN(C1C=CC=CN=1)C.[NH2:37][C:38]1[N:47]=[C:46]([C:48]([N:50]2[CH2:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH2:51]2)=[O:49])[C:45]2[C:40](=[CH:41][CH:42]=[C:43]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=3[S:65](N(CCO)C)(=[O:67])=[O:66])[CH:44]=2)[N:39]=1>C1COCC1>[NH2:8][CH2:9][C:10]([O:12][CH2:14][CH2:13][NH:19][CH2:20][S:65]([C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=1[C:43]1[CH:44]=[C:45]2[C:40](=[CH:41][CH:42]=1)[N:39]=[C:38]([NH2:37])[N:47]=[C:46]2[C:48]([N:50]1[CH2:51][C:52]2[C:57](=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:58]1)=[O:49])(=[O:66])=[O:67])=[O:11]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 46701881HCID 46701881, compound

Product 1

HCID 67434865HCID 67434865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

56 mg of tert-butoxycarbonylaminoacetic acid, 33 mg of N,N′-dicyclohexylcarbodiimide and 2 mg of dimethylaminopyridine (DMAP) are added to a solution of 80 mg of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide in 1 ml of THF. After 120 min, the mixture is evaporated in vacuo, the residue is taken up in 1 ml of DCM:TFA (1:1) with cooling, and the mixture is stirred for 30 min. The mixture is evaporated to dryness in vacuo, the residue is taken up in 500 μl of DMSO and purified by column chromatography on a reversed phase.

Workup

  1. customthe mixture is evaporated in vacuo
  2. temperaturewith cooling
  3. customThe mixture is evaporated to dryness in vacuo
  4. custompurified by column chromatography on a reversed phase

Sources & evidence

ORD record
ord-bb3fe785e187407a950f8d9f90ad0f06
Source dataset
uspto-grants-2013_10
Patent number
US08546565B2

Reaction notes

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