Diisopropylethylamine → 1-(2-{6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetyl)-azetidine-3-carboxylic acid methyl ester

HRID 2063572Notes

Reaction equation

HRID 2063572 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][C:25]4[CH:29]=[CH:28][N:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:26]=4)[CH2:19][CH2:18]3)[C:11]=1[O:12][CH2:13][C:14](O)=[O:15])[N:8]=[CH:7][CH:6]=[CH:5]2.Cl.[CH3:37][O:38][C:39]([CH:41]1[CH2:44][NH:43][CH2:42]1)=[O:40].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:37][O:38][C:39]([CH:41]1[CH2:44][N:43]([C:14](=[O:15])[CH2:13][O:12][C:11]2[C:10]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][C:25]4[CH:29]=[CH:28][N:27]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:26]=4)[CH2:19][CH2:18]3)=[C:9]3[C:4]([CH:5]=[CH:6][CH:7]=[N:8]3)=[CH:3][C:2]=2[CH3:1])[CH2:42]1)=[O:40]

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 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 59366173HCID 59366173, compound

Product 1

HCID 593661781-(2-{6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetyl)-azetidine-3-carboxylic acid methyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid (100 mg, 0.21 mmol), 3-Azetidinecarboxylic methyl ester HCl salt (35.4 mg, 0.23 mmol), HATU (97 mg, 0.25 mmol) and DIEA (0.222 ml) in DMF (1 ml) was stirred at rt for 2 hrs. After an aqueous workup, the mixture was purified by flash chromatography to give a light yellow solid (70 mg, 59%). MS (ES) m/z 569.3 (M+H+).

Workup

  1. customAfter an aqueous workup, the mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-3d93165ca6544e998f7e722d10c0054c
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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