Triethylamine → HCID 89579668, compound

HRID 928623Notes

Reaction equation

HRID 928623 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]1[CH2:12][CH:11]2[N:13]([C:14]3[C:15]4[C:22]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[C:21]([C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[O:30])[S:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:8]([CH2:9][CH2:10]2)[CH2:7]1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[CH:32]([NH:31][C:29]([C:21]1[S:20][C:16]2[N:17]=[CH:18][N:19]=[C:14]([N:13]3[CH:11]4[CH2:10][CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][O:4][CH2:3][CH2:2][NH:1][S:43]([CH3:42])(=[O:45])=[O:44])[CH2:12]4)[C:15]=2[C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:30])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 89579681HCID 89579681, compound

Product 1

HCID 89579668HCID 89579668, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(2-aminoethoxymethyl)-8-azabicyclo[3.2.1]octan-8-yl]-N-isopropyl-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide (0.1 g, 0.2 mmol) and was stirred in DCM (10 mL) at 0° C. Triethylamine (0.04 g, 0.06 mL, 0.4 mmol) was added followed by methanesulfonyl chloride (0.04 g, 0.02 mL, 0.3 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The solvent was removed at reduced pressure. The resulting residue was taken up in DCM, washed with water, dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by acidic prep HPLC (method 1). Desired fractions were combined and concentrated at reduced pressure. The residue was taken up in DCM, washed with sat. NaHCO3 solution, the organic dried over Na2SO4 and concentrated at reduced pressure to afford N-isopropyl-4-[3-[2-(methanesulfonamido)ethoxymethyl]-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxamide (41 mg).

Workup

  1. customThe solvent was removed at reduced pressure
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. customThe resulting residue was purified by acidic prep HPLC (method 1)
  6. concentrationconcentrated at reduced pressure
  7. washwashed with sat. NaHCO3 solution
  8. dry with materialthe organic dried over Na2SO4
  9. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-e749e9a48ed34f349ea45e27830613e2
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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