Methyl chloroformate → HCID 86708580, compound

HRID 1430883Notes

Reaction equation

HRID 1430883 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([Cl:31])=[C:10]([NH:16][C:17]3[N:22]=[C:21]([NH:23][CH2:24][CH3:25])[C:20]4=[N:26][CH:27]=[C:28]([C:29]#[N:30])[N:19]4[N:18]=3)[CH:11]=[C:12]([C:14]#[N:15])[CH:13]=2)[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[C:41](Cl)(=[O:44])[O:42][CH3:43]>CO.C1COCC1>[Cl:31][C:9]1[C:10]([NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH3:25])[C:20]3=[N:26][CH:27]=[C:28]([C:29]#[N:30])[N:19]3[N:18]=2)=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:41](=[O:44])[O:42][CH3:43])[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 86708581HCID 86708581, compound

Product 1

HCID 86708580HCID 86708580, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-((3-(4-aminopiperidin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 329) (40 mg, 0.092 mmol) was mixed with N,N-diisopropylethylamine (0.2 ml, 1.145 mmol) in MeOH (1 ml) and THF (1 ml). methyl carbonochloridate (0.05 ml, 0.646 mmol) was added. The mixture was stirred at r.t. for 1 hr. LC/MS showed product formation. The white precipitate was formed and collected by filtration, washed with cold MeOH (15 ml), then water (5 ml) and dried with air-suction to give 31.7 mg of desired product.

Workup

  1. customThe white precipitate was formed
  2. filtrationcollected by filtration
  3. washwashed with cold MeOH (15 ml)
  4. dry with materialwater (5 ml) and dried with air-suction

Sources & evidence

ORD record
ord-3bf7629133ad47c5a59d7deb5216c5d0
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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