Diisopropylethylamine → HCID 66669378, compound

HRID 2106173Notes

Reaction equation

HRID 2106173 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2([C:28](O)=[O:29])[CH2:27][CH2:26]2)=[O:24])=[CH:18][CH:17]=1.[C:31]([O:35][C:36](=[O:46])[NH:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42](N)=[CH:41][CH:40]=1)([CH3:34])([CH3:33])[CH3:32].C[N:48](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CC(N(C)C)=O>[C:31]([O:35][C:36](=[O:46])[NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([NH:48][C:28]([C:25]2([C:23](=[O:24])[NH:22][C:19]3[CH:18]=[CH:17][C:16]([O:15][C:6]4[C:5]5[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=[CH:8][CH:7]=4)=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)=[O:29])[CH:40]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57810164849217-77-2

Product 1

HCID 66669378HCID 66669378, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

1-[4-(6,7-Dimethoxy-quinolin-4-yloxy)-phenylcarbamoyl]-cyclopropanecarboxylic acid (254 mg, 0.62 mmol), (4-amino-benzyl)-carbamic acid tert-butyl ester (164 mg, 0.74 mmol), dry DMA (10 mls), HATU (714 mg, 1.88 mmol), and DIEA (325 ml, 1.86 mmol) were combined and stirred at room temperature. After 2 hrs, the reaction mixture is diluted with H2O and the resulting solids are filtered, washed with H2O, followed by sat'd NaHCO3, and dried under high vacuum to give crude [3-({1-[4-(6,7-dimethoxy-quinolin-4-yloxy)-phenylcarbamoyl]-cyclopropanecarbonyl}-amino)-benzyl]-carbamic acid tert-butyl ester (301 mg, 79% yield) which was used in the next reaction without further purification. LC/MS Calcd for [M+H]+ 613.3, found 613.1.

Workup

  1. filtrationthe resulting solids are filtered
  2. washwashed with H2O
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-d9323be320e34b1b86e84cfdd26efce8
Source dataset
uspto-grants-2009_08
Patent number
US07579473B2

Reaction notes

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