Trifluoroacetic acid → HCID 59605548, compound

HRID 1923349Notes

Reaction equation

HRID 1923349 reaction equation
C(OC(=O)[NH:7][C:8]1([C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[N:21]([CH3:46])[C:22]4[C:27]([N:28]=3)=[C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:25]=[C:24]([N:35]3[C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=5[N:37]=[C:36]3[CH2:44][CH3:45])[N:23]=4)[C:15]([CH3:48])([CH3:47])[CH2:14]2)=[O:12])[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1([C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[N:21]([CH3:46])[C:22]4[C:27]([N:28]=3)=[C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:25]=[C:24]([N:35]3[C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=5[N:37]=[C:36]3[CH2:44][CH3:45])[N:23]=4)[C:15]([CH3:47])([CH3:48])[CH2:14]2)=[O:12])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605613HCID 59605613, compound

Product 1

HCID 59605548HCID 59605548, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-{4-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl]-3,3-dimethylpiperazine-1-carbonyl}cyclopropyl)carbamic acid tert-butyl ester in DCM (3 mL) was added TFA (2 mL) and the resulting mixture stirred at r.t. for 30 min then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si-PCC, MeOH:DCM, 0-10%) affording 780 as a white foam (99 mg, 60%). LCMS (method I): RT 2.67 min, [M+H]+ 573.3. 1H NMR (CDCl3, 400 MHz): δ 8.02-8.01 (1 H, m), 7.76-7.75 (1 H, m), 7.32-7.22 (2 H, m), 4.34 (4 H, s), 3.93 (3 H, s), 3.88-3.86 (6 H, m), 3.65 (2 H, s), 3.48 (2 H, s), 3.36 (2 H, q, J=7.48 Hz), 2.57 (2 H, t, J=5.16 Hz), 1.85-1.75 (2 H, brd s), 1.45 (3 H, t, J=7.46 Hz), 1.23 (6 H, s), 1.05-0.99 (2 H, m), 0.81-0.80 (2 H, m)

Workup

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH
  3. customThe resulting residue was purified by column chromatography (Si-PCC, MeOH:DCM, 0-10%)

Sources & evidence

ORD record
ord-f65c6d81f48c4649b22079e15f310850
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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