Acetic Acid → HCID 86708689, compound

HRID 1430972Notes

Reaction equation

HRID 1430972 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:6][C:5]([C:14]#[N:15])=[CH:4][C:3]=1[NH:16][C:17]1[N:22]=[C:21]([N:23]([CH:33]2[CH2:35][CH2:34]2)CC2C=CC(OC)=CC=2)[C:20]2=[N:36][CH:37]=[C:38]([C:39]#[N:40])[N:19]2[N:18]=1.[O:41]1[CH2:44][C:43](=O)[CH2:42]1.C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCl.CO>[Cl:1][C:2]1[C:7]([O:8][CH:9]2[CH2:13][CH2:12][N:11]([CH:43]3[CH2:44][O:41][CH2:42]3)[CH2:10]2)=[CH:6][C:5]([C:14]#[N:15])=[CH:4][C:3]=1[NH:16][C:17]1[N:22]=[C:21]([NH:23][CH:33]2[CH2:35][CH2:34]2)[C:20]2=[N:36][CH:37]=[C:38]([C:39]#[N:40])[N:19]2[N:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 86708690HCID 86708690, compound

Product 1

HCID 86708689HCID 86708689, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (+/−)-2-((2-chloro-5-cyano-3-(pyrrolidin-3-yloxy)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (36 mg, 0.065 mmol), oxetan-3-one (8.30 μl, 0.129 mmol), acetic acid (7.41 μl, 0.129 mmol) and molecular sieves (30 mg) in dichloromethane (1 mL)/Methanol (1 mL) was stirred at room temperature overnight. sodium cyanoborohydride (12.21 mg, 0.194 mmol) was added and the reaction mixture was stirred for 1 h. The reaction mixture was filtered through a plug of celite and the filtrate was concentrated. The crude product (38 mg) was used without purification.

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. filtrationThe reaction mixture was filtered through a plug of celite
  3. concentrationthe filtrate was concentrated
  4. customThe crude product (38 mg) was used without purification

Sources & evidence

ORD record
ord-a6978cab820b4f349fcf527c69281f7d
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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