Diisopropylethylamine → (5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-(2,2-dimethyl-4-oxetan-3-ylpiperazin-1-yl)methanone

HRID 1922767Notes

Reaction equation

HRID 1922767 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:10]=[C:9]([C:11]([OH:13])=O)[S:8][C:6]=2[N:7]=1.[CH3:20][C:21]1([CH3:31])[NH:26][CH2:25][CH2:24][N:23]([CH:27]2[CH2:30][O:29][CH2:28]2)[CH2:22]1.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>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:10]=[C:9]([C:11]([N:26]3[CH2:25][CH2:24][N:23]([CH:27]4[CH2:30][O:29][CH2:28]4)[CH2:22][C:21]3([CH3:31])[CH3:20])=[O:13])[S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 674922623,3-Dimethyl-1-(oxetan-3-yl)piperazineHCID 866482365-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid

Product 1

HCID 59606073(5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-(2,2-dimethyl-4-oxetan-3-ylpiperazin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid (100 mg, 0.33 mmol), 3,3-dimethyl-1-oxetan-3-ylpiperazine (62 mg, 0.36 mmol), HATU (278 mg, 0.37 mmol) and DIPEA (65 μL, 0.37 mmol) in DCM (3 mL) was allowed to stir at r.t. for 18 h. The reaction mixture was concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 0-2%) affording the title compound as a yellow solid. LCMS (method H): RT 2.67 min, [M+H]+ 453.3

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 0-2%)

Sources & evidence

ORD record
ord-4689b8d2214545a6a52847b5cc6b4095
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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