Triethylamine → HCID 59605434, compound

HRID 1922781Notes

Reaction equation

HRID 1922781 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:9]=[C:10]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:11]3[N:16]=[C:15]([CH2:17][CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[S:14][C:12]=3[N:13]=2)[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=2[N:4]=1)[CH3:2].Cl[C:35]([C:37]([O:40][C:41](=[O:43])[CH3:42])([CH3:39])[CH3:38])=[O:36].CCN(CC)CC>C(Cl)Cl>[CH2:1]([C:3]1[N:7]([C:8]2[N:9]=[C:10]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:11]3[N:16]=[C:15]([CH2:17][CH:18]4[CH2:19][CH2:20][N:21]([C:35](=[O:36])[C:37]([O:40][C:41](=[O:43])[CH3:42])([CH3:39])[CH3:38])[CH2:22][CH2:23]4)[S:14][C:12]=3[N:13]=2)[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 59606106HCID 59606106, compound

Product 1

HCID 59605434HCID 59605434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(2-ethylbenzoimidazol-1-yl)-7-morpholin-4-yl-2-piperidin-4-ylmethylthiazolo[5,4-d]pyrimidine (96 mg, 0.21 mmol), acetic acid 1-chlorocarbonyl-1-methylethyl ester (40 μL, 0.28 mmol) and NEt3 (40 μL, 0.31 mmol) in DCM (1 mL) was allowed to stir at r.t. for 30 min then concentrated in vacuo. The resulting residue was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH affording Acetic acid 2-{4-[5-(2-ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-ylmethyl]piperidin-1-yl}-1,1-dimethyl-2-oxoethyl ester. LCMS (method A): RT 3.19 min [M+H]+ 592.2

Workup

  1. concentrationthen concentrated in vacuo
  2. washwas washed with MeOH
  3. washthe product eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-5f5662a4549442f2a17927fa7575d182
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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