Diisopropylethylamine → Tert-butyl 3-(6-(6-(4-hydroxybenzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamido)-2,2-dimethylpropylcarbamate

HRID 469275Notes

Reaction equation

HRID 469275 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:40]=[CH:39][C:14]([CH2:15][NH:16][C:17]2[N:22]=[C:21]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[N:20]=[C:19]([NH:29][C:30]3[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][N:31]=3)[CH:18]=2)=[CH:13][CH:12]=1.[NH2:41][CH2:42][C:43]([CH3:54])([CH3:53])[CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[OH:10][C:11]1[CH:40]=[CH:39][C:14]([CH2:15][NH:16][C:17]2[N:22]=[C:21]([O:23][CH2:24][C:25]([F:28])([F:26])[F:27])[N:20]=[C:19]([NH:29][C:30]3[CH:38]=[CH:37][C:33]([C:34]([NH:41][CH2:42][C:43]([CH3:54])([CH3:53])[CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:51])[CH3:50])=[O:35])=[CH:32][N:31]=3)[CH:18]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 4114359tert-butyl N-(3-amino-2,2-dimethylpropyl)carbamateHCID 866793196-((6-((4-Hydroxybenzyl)amino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-yl)amino)nicotinic acid

Product 1

HCID 86679318Tert-butyl 3-(6-(6-(4-hydroxybenzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamido)-2,2-dimethylpropylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

iPr2NEt (0.5 mL) was added into a solution of 6-((6-((4-hydroxybenzyl)amino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-yl)amino)nicotinic acid (340 mg), tert-butyl (3-amino-2,2-dimethylpropyl)carbamate (316 mg) and TBTU (501 mg) in THF (10 mL). The reaction was stirred at room temperature for 16 hours before being quenched by water (10 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic phase was dried over MgSO4 and concentrated under vacuum to give the crude product, tert-butyl 3-(6-(6-(4-hydroxybenzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamido)-2,2-dimethylpropylcarbamate, which was purified by silica gel chromatography.

Workup

  1. custombefore being quenched by water (10 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-eccbded747cb4e63881c1264bac01564
Source dataset
uspto-grants-2014_01
Patent number
US08629150B2

Reaction notes

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