Diisopropylethylamine → HCID 24812352, compound

HRID 573486Notes

Reaction equation

HRID 573486 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[N:8]=[C:7]1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][C:20]=1[F:26])C.[CH3:28][C:29]([N:36]1[CH2:41][CH2:40][CH:39]([NH:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:55]=[CH:54][C:53]([C:56]([F:59])([F:58])[F:57])=[CH:52][CH:51]=3)=[CH:46][CH:45]=2)[CH2:38][CH2:37]1)([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:77][P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:26][C:20]1[C:21]([F:77])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][C:7]1[N:6]([CH2:5][C:4]([N:42]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:51]=[CH:52][C:53]([C:56]([F:58])([F:57])[F:59])=[CH:54][CH:55]=3)=[CH:46][CH:45]=2)[CH:39]2[CH2:38][CH2:37][N:36]([C:29]([CH3:28])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:41][CH2:40]2)=[O:3])[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[N:8]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59264610HCID 59264610, compoundHCID 59707037Ethyl[2-[2-(2,4-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]acetate

Product 1

HCID 24812352HCID 24812352, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [2-[2-(2,3-difluorophenyl)ethyl]-4-oxo-1(4H)-quinazolinyl]acetic acid (Int. C1) (115 mg, 1 equiv), ethyl 2-methyl-2-[4-({[4′-(trifluoromethyl)-4-biphenylyl]methyl}amino)-1-piperidinyl]propanoate (Int. B2) (150 mg, 1 equiv), HATU (151 mg, 1.2 equiv), DMF (2.7 ml) and DIPEA (0.17 ml, 3 equiv) was shaken at room temperature for 5 h. The reaction mixture was partitioned between ethyl acetate/methanol and aqueous sodium bicarbonate, then the organic layer was brine-washed and dried. Flash chromatography (silica, 3-4% methanol in DCM) gave ethyl 2-[4-({[2-[2-(2,3-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]acetyl}{[4′-(trifluoromethyl)-4-biphenylyl]methyl}amino)-1-piperidinyl]-2-methylpropanoate as a white solid (190 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate/methanol and aqueous sodium bicarbonate
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-ccb9cce612e947919359fa2d8e28e4cd
Source dataset
uspto-grants-2015_05
Patent number
US09029383B2

Reaction notes

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