Triethylamine → HCID 59254929, compound

HRID 2194999Notes

Reaction equation

HRID 2194999 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[C:16]1[N:25]=[CH:24][C:23]2[CH2:22][CH2:21][C:20]3[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:19]=3[C:18]=2[N:17]=1.C(N(CC)CC)C.[CH:40]([N:43]=[C:44]=[O:45])([CH3:42])[CH3:41]>C(#N)C>[CH:40]([NH:43][C:44]([N:13]1[CH2:12][CH2:11][CH:10]([C:9]#[C:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:16]3[N:25]=[CH:24][C:23]4[CH2:22][CH2:21][C:20]5[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:19]=5[C:18]=4[N:17]=3)[CH:4]=2)[CH2:15][CH2:14]1)=[O:45])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 59254925HCID 59254925, compound

Product 1

HCID 59254929HCID 59254929, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

50 mg (0.11 mmol) N-[8-(2-chloro-5-piperidin-4-ylethynyl-phenyl)-4,5-dihydrothiazolo[4,5-h]quinazolin-2-yl]-acetamide are suspended in 1 mL acetonitrile and combined successively with 17 μL triethylamine and 22 μM isopropyl isocyanate. The yellow suspension is stirred for three hours at ambient temperature and then washed with aqueous potassium carbonate solution. The organic phase is evaporated down and the residue is purified by RP-HPLC. Yield: 30 mg yellow solid.

Workup

  1. washwashed with aqueous potassium carbonate solution
  2. customThe organic phase is evaporated down
  3. customthe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-beeb7653f5ca4fc18534f750577709bf
Source dataset
uspto-grants-2012_12
Patent number
US08334378B2

Reaction notes

Loading…