Diisopropylethylamine → HCID 68052027, compound

HRID 1428260Notes

Reaction equation

HRID 1428260 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.ClC(Cl)(O[C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.[N:34]1([C:43]2[C:44]3[CH:51]=[CH:50][NH:49][C:45]=3[N:46]=[CH:47][N:48]=2)[C@H:42]2[C@H:37]([NH:38][CH2:39][CH2:40][CH2:41]2)[CH2:36][CH2:35]1>C(Cl)Cl>[N:46]1[C:45]2[NH:49][CH:50]=[CH:51][C:44]=2[C:43]([N:34]2[C@H:42]3[C@H:37]([N:38]([C:26]([NH:1][CH2:2][C:3]4[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=4)=[O:32])[CH2:39][CH2:40][CH2:41]3)[CH2:36][CH2:35]2)=[N:48][CH:47]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 571728Methyl 4-(aminomethyl)benzoateHCID 56967819HCID 56967819, compound

Product 1

HCID 68052027HCID 68052027, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 4-(aminomethyl)benzoate (25 mg, 0.12 mmol), was added DCM (376 μL), DIPEA (43 μL, 0.25 mmol) and triphosgene (11 mg, 0.037 mmol) at 0° C. The reaction was stirred for 2.5 hours before 4-[(3aR,7aR)-octahydro-1H-pyrrolo[3,2-b]pyridin-1-yl]-7H-pyrrolo[2,3-d]pyrimidine (30.2 mg, 0.124 mmol) was added. The resulting solution was stirred for an additional 3 hours before being concentrated in vacuo and purified by mass triggered reverse phase HPLC. Lyophilization of the desired fractions gave the title compound (TFA salt) as a white solid. LRMS calc'd for C23H27N6O3 [M+H]+, 435; found 435. Jak1 activity: ++.

Workup

  1. additionwas added
  2. concentrationbefore being concentrated in vacuo
  3. custompurified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-2095a06106f542809f36bf432dd39752
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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