Triethylamine → HCID 59605520, compound

HRID 1946180Notes

Reaction equation

HRID 1946180 reaction equation
[NH:1]1[CH2:4][CH:3]([CH2:5][C:6]2[N:7]([CH3:32])[C:8]3[C:13]([N:14]=2)=[C:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:11]=[C:10]([N:21]2[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=[C:22]2[CH2:30][CH3:31])[N:9]=3)[CH2:2]1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1.CCN(CC)CC>C(Cl)Cl>[CH:33]1([C:36]([N:1]2[CH2:2][CH:3]([CH2:5][C:6]3[N:7]([CH3:32])[C:8]4[C:13]([N:14]=3)=[C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:11]=[C:10]([N:21]3[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[N:23]=[C:22]3[CH2:30][CH3:31])[N:9]=4)[CH2:4]2)=[O:37])[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 596052818-Azetidin-3-ylmethyl-2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine

Product 1

HCID 59605520HCID 59605520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-azetidin-3-ylmethyl-2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine (108 mg, 0.25 mmol), cyclopropane carbonyl chloride (27 mg, 0.25 mmol) and NEt3 (50 μL, 0.36 mmol) in DCM (1 mL) was allowed to stir at r.t. for 2 h then concentrated in vacuo. The resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) followed by triturating with Et2O affording 825 as a white solid (107 mg, 85%). LCMS (method I): RT 3.33 min, [M+H]+ 501.2. 1H NMR (CDCl3, 400 MHz): δ 7.99-7.98 (1 H, m), 7.76-7.73 (1 H, m), 7.32-7.22 (2 H, m), 4.53 (1 H, t, J=8.31 Hz), 4.45-4.20 (4 H, brd s), 4.28 (1 H, t, J=9.30 Hz), 4.09 (1 H, dd, J=8.45, 5.41 Hz), 3.86 (5 H, t, J=4.77 Hz), 3.77 (3 H, s), 3.34-3.33 (3 H, m), 3.18-3.15 (2 H, m), 1.45-1.43 (4 H, m), 0.99-0.98 (2 H, m), 0.77-0.76 (2 H, m)

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%)
  3. customby triturating with Et2O affording 825 as a white solid (107 mg, 85%)
  4. customRT 3.33 min, [M+H]+ 501.2

Sources & evidence

ORD record
ord-a91298903e344924ad85873146de2bdb
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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