Cyclopropanecarbonyl chloride → HCID 66628430, compound

HRID 2200965Notes

Reaction equation

HRID 2200965 reaction equation
Cl.[NH2:2][C:3]1[N:36]=[C:6]2[N:7]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:8]([CH3:25])=[C:9]([C:23]#[N:24])[C@@H:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=3[S:19]([CH3:22])(=[O:21])=[O:20])[N:5]2[N:4]=1.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1>N1C=CC=CC=1>[C:23]([C:9]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=2[S:19]([CH3:22])(=[O:21])=[O:20])[N:5]2[N:4]=[C:3]([NH:2][C:40]([CH:37]3[CH2:39][CH2:38]3)=[O:41])[N:36]=[C:6]2[N:7]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=2)[C:8]=1[CH3:25])#[N:24]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 66628313HCID 66628313, compound

Product 1

HCID 66628430HCID 66628430, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under an atmosphere of argon protective gas, (7S)-2-amino-7-[4-cyano-2-(methylsulfonyl)phenyl]-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile hydrochloride (16 mg, 30 μmol) was dissolved in abs. pyridine (1 ml). At room temperature, cyclopropanecarbonyl chloride was added in two portions (in each case 3.7 mg, 36 μmol, 1.2 eq.). Once HPLC showed substantial conversion (12 h), the reaction mixture was concentrated under reduced pressure and purified by preparative HPLC (Macherey & Nagel Gravity C18 column, 21×300 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (11.2 mg, 66% of theory).

Workup

  1. customconversion (12 h)
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. custompurified by preparative HPLC (Macherey & Nagel Gravity C18 column, 21×300 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (11.2 mg, 66% of theory)

Sources & evidence

ORD record
ord-41e4b0840c2942c987deb188d9d0f113
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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