Triethylamine → HCID 86708500, compound

HRID 1430821Notes

Reaction equation

HRID 1430821 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:14]([Cl:37])=[C:15]([NH:21][C:22]3[N:27]=[C:26]([NH:28][CH:29]4[CH2:31][CH2:30]4)[C:25]4=[N:32][CH:33]=[C:34]([C:35]#[N:36])[N:24]4[N:23]=3)[CH:16]=[C:17]([C:19]#[N:20])[CH:18]=2)[CH2:9][C@H:8]1[O:38][Si:39]([CH:46]([CH3:48])[CH3:47])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41].C(N(CC)CC)C>ClCCl>[Cl:37][C:14]1[C:15]([NH:21][C:22]2[N:27]=[C:26]([NH:28][CH:29]3[CH2:30][CH2:31]3)[C:25]3=[N:32][CH:33]=[C:34]([C:35]#[N:36])[N:24]3[N:23]=2)=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=1[N:10]1[CH2:11][CH2:12][C@@H:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[C@H:8]([O:38][Si:39]([CH:43]([CH3:45])[CH3:44])([CH:46]([CH3:48])[CH3:47])[CH:40]([CH3:41])[CH3:42])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86708497HCID 86708497, compound

Product 1

HCID 86708500HCID 86708500, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (7.5 μl, 0.10 mmol) was added to a solution of 2-((3-((3R,4R)-4-amino-3-((triisopropylsilyl)oxy)piperidin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (25 mg, 0.040 mmol) and triethylamine (17 μl, 0.120 mmol) in dichloromethane (1 mL) and the reaction solution was stirred at room temperature overnight. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (12 g column, eluting with 0-40% ethyl acetate/dichloromethane). N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-((triisopropylsilyl)oxy)piperidin-4-yl)methanesulfonamide (28 mg) was obtained as a white solid.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel using
  2. washan automated ISCO system (12 g column, eluting with 0-40% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-7a30c284ceaf491494e4934e13d012b3
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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