Diisopropylethylamine → HCID 59605982, compound

HRID 1923375Notes

Reaction equation

HRID 1923375 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[S:10][C:11]2[N:12]=[C:13]([N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[N:26]=[C:25]3[CH2:33][CH3:34])[N:14]=[C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:16]=2[N:17]=1.[C:36](O)(=[O:40])[C@H:37]([CH3:39])[OH:38].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:33]([C:25]1[N:24]([C:13]2[N:14]=[C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:16]3[N:17]=[C:9]([CH2:8][N:3]4[CH2:4][CH2:5][N:6]([C:36](=[O:40])[C@@H:37]([OH:38])[CH3:39])[CH2:7][C:2]4([CH3:35])[CH3:1])[S:10][C:11]=3[N:12]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=1)[CH3:34]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67492436HCID 67492436, compound

Product 1

HCID 59605982HCID 59605982, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2,2-dimethylpiperazin-1-ylmethyl)-5-(2-ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine (200 mg, 0.41 mmol), L-lactic acid (34 μL, 85% solution in H2O), HATU (170 mg, 0.45 mmol) and DIPEA (80 μL, 0.46 mmol) in DCM (4 mL) was allowed to stir at r.t. for 3 h. The reaction mixture was 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:EtOAc, 0-2%) then (C18, MeOH:H2O, 10-20%). 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 829 (41 mg, 18%). LCMS (method I): RT 3.79 min, [M+H]+ 565.3. 1H NMR (CDCl3, 400 MHz): δ 8.03-7.98 (1 H, m), 7.76-7.75 (1 H, m), 7.32-7.22 (2 H,m), 4.41-4.38 (5 H, m), 4.08-4.01 (1 H, m), 3.89-3.88 (5 H, m), 3.79-3.77 (1 H, m), 3.59-3.44 (2 H, m), 3.34 (2 H, q, J=7.47 Hz), 3.27-3.25 (1 H, m), 2.75 (2 H, s), 1.44 (3 H, t, J=7.47 Hz), 1.37-1.35 (3 H, m), 1.27-1.11 (6 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:EtOAc, 0-2%)
  4. washwas washed with MeOH
  5. washthe product eluted with 2M NH3/MeOH affording 829 (41 mg, 18%)
  6. customRT 3.79 min, [M+H]+ 565.3

Sources & evidence

ORD record
ord-9b3c9e37e5794770831030b50ad2dc66
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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