Diisopropylethylamine → HCID 59605655, compound

HRID 1945611Notes

Reaction equation

HRID 1945611 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[N:10]=[C:9]([CH2:11][C:12]([OH:14])=O)[S:8][C:6]=2[N:7]=1.[CH3:21][C:22]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([CH3:25])[CH2:23][OH:24].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>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[N:10]=[C:9]([CH2:11][C:12]([N:29]3[CH2:30][CH2:31][N:26]([C:22]([CH3:25])([CH3:21])[CH2:23][OH:24])[CH2:27][CH2:28]3)=[O:14])[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 120525542-Methyl-2-(piperazin-1-yl)propan-1-olHCID 86648235HCID 86648235, compound

Product 1

HCID 59605655HCID 59605655, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)acetic acid (80 mg, 0.25 mmol), 2-methyl-2-piperazin-1-ylpropan-1-ol (48 mg, 0.31 mmol), HATU (116 mg, 0.31 mmol) and DIPEA (133 μL, 0.76 mmol) in DMF (3 mL) was stirred at r.t. for 65 h then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH/DCM. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as an orange solid (65 mg, 56%). LCMS (method H): RT 2.02 min [M+H]+ 455.3

Workup

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

Sources & evidence

ORD record
ord-7378ca6ed5cc49b6901a4a9fa6302e88
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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