Diisopropylethylamine → HCID 86694436, compound

HRID 1428263Notes

Reaction equation

HRID 1428263 reaction equation
[N:1]1([C:10]2[C:11]3[CH:18]=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[C@H:9]2[C@H:4]([NH:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH:28]([S:31](Cl)(=[O:33])=[O:32])([CH3:30])[CH3:29]>C(#N)C.CN(C1C=CN=CC=1)C.CS(C)=O>[CH3:29][CH:28]([S:31]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:9]2[N:1]([C:10]3[C:11]4[CH:18]=[CH:17][NH:16][C:12]=4[N:13]=[CH:14][N:15]=3)[CH2:2][CH2:3][C@@H:4]12)(=[O:33])=[O:32])[CH3:30]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 824082-Propanesulfonyl chlorideHCID 56967819HCID 56967819, compound

Product 1

HCID 86694436HCID 86694436, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-[(3aR,7aR)-octahydro-1H-pyrrolo[3,2-b]pyridin-1-yl]-7H-pyrrolo[2,3-d]pyrimidine (12 mg, 0.049 mmol) in acetonitrile (493 tip was added DMAP (9.0 mg, 0.074 mmol) and DIPEA (17 μL, 0.099 mmol) followed by isopropylsulfonyl chloride (12 mg, 0.049 mmol). The reaction mixture was stirred for 20 hours at room temperature before being diluted with 1.0 mL DMSO and purified by mass-triggered reverse-phase HPLC using a Waters X-bridge Prep C18 column (5 micron, 19×100 mm), eluting with an ACN/water gradient (0.1% formic acid as modifier) to afford 4-{(3aR,7aR)-4-[(1-methylethyl)sulfonyl]octahydro-1H-pyrrolo[3,2-b]pyridin-1-yl}-7H-pyrrolo[2,3-d]pyrimidine. LRMS calc'd for C16H24N5O2S [M+H]+, 350.2; found 350.2. 1H NMR (500 MHz, DMSO-D6) δ 11.6 (s, 1H); 8.04 (s, 1H); 7.09 (s, 1H), 6.51 (s, 2H); 4.29 (br s, 2H); 3.97-3.64 (br m, 21-1); 3.53 (d, 2H, J=11Hz); 3.38-3.34 (m, 1H); 3.02 (t, 1H. J=10Hz); 2.01 (br s, 1H); 1.64 (s, 1H), 1.62 (br s, 1H), 1.24-1.54 (br m, 2H). 1.21 (t, 6H, J=5.5Hz). Jak1 activity: ++

Workup

  1. custompurified by mass-triggered reverse-phase
  2. washeluting with an ACN/water gradient (0.1% formic acid as modifier)

Sources & evidence

ORD record
ord-85eae59a4426411e9987c0b4c545f1cd
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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