Dichloromethane → HCID 67355292, compound

HRID 627445Notes

Reaction equation

HRID 627445 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([N:22]5[C:29](=[O:30])[CH2:28][C@@H:27]6[NH:31][C@@H:24]([CH2:25][CH2:26]6)[CH2:23]5)=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:37](OC(=O)C)(=[O:39])[CH3:38].C(N(C(C)C)CC)(C)C.C(Cl)Cl>CCOC(C)=O>[C:37]([N:31]1[C@@H:27]2[CH2:26][CH2:25][C@H:24]1[CH2:23][N:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:12]3[N:13]=[CH:14][C:9]4[CH:8]=[C:7]([C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[N:6]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)[C:10]=4[N:11]=3)=[N:17][CH:18]=1)[C:29](=[O:30])[CH2:28]2)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 53377611HCID 53377611, compound

Product 1

HCID 67355292HCID 67355292, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A sample of 7-Cyclopentyl-N,N-dimethyl-2-(5-((1S,6R)-4-oxo-3,9-diazabicyclo[4.2.1]nonan-3-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (50 mg, 0.102 mmol), acetic anhydride (0.020 ml, 0.113 mmol) and diisopropylethylamine (0.014 ml, 0.154 mmol) were combined with 1 ml DCM. The mixture was allowed to stir for 16 hr and then taken up into EtOAc, washed with brine, dried over Na2SO4 filtered and concentrated. The crude product was purified by silica gel chromatography which gave 2-(5-((1S,6R)-9-acetyl-4-oxo-3,9-diazabicyclo[4.2.1]nonan-3-yl)pyridin-2-ylamino)-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (32 mg) 52% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.70 (d, J=8.08 Hz, 1H), 8.82 (s, 1H), 8.33 (dd, J=9.09, 6.06 Hz, 1H), 8.13 (d, J=2.53 Hz, 1H), 7.60 (dd, J=9.09, 2.53 Hz, 1H), 6.63 (s, 1H), 4.76 (t, J=8.84 Hz, 1H), 4.70 (br. s., 0H), 4.55 (m, 0H), 4.43 (s, 0H), 4.34 (br. s., 0H), 4.18 (d, J=14.65 Hz, 0H), 4.06 (d, J=14.15 Hz, 0H), 3.59 (m, 1H), 3.06 (br. s., 6H), 2.98 (d, J=16.17 Hz, 1H), 2.87 (d, J=14.65 Hz, 0H), 2.73 (m, 1H), 2.44 (br. s., 2H), 2.19 (m, 1H), 2.05 (d, J=4.55 Hz, 3H), 1.98 (m, 6H), 1.82 (m, 2H), 1.66 (d, J=5.56 Hz, 3H), 1.23 (br. s., 1H). MS m/z 531.6 (M+H).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography which

Sources & evidence

ORD record
ord-97018c16f717487a9f8976de222003f5
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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