HCID 67355731, compound → HCID 67356908, compound

HRID 1850550Notes

Reaction equation

HRID 1850550 reaction equation
C(OC([N:11]1[CH2:17][CH:16]2[N:18]([C:19]([C:21]3[CH:22]=[N:23][C:24]([NH:27][C:28]4[N:29]=[CH:30][C:31]5[CH:36]=[C:35]([C:37](=[O:41])[N:38]([CH3:40])[CH3:39])[N:34]([CH:42]6[CH2:46][CH2:45][CH2:44][CH2:43]6)[C:32]=5[N:33]=4)=[CH:25][CH:26]=3)=[O:20])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1)=O)C1C=CC=CC=1>[Pd]>[CH3:39][N:38]([CH3:40])[C:37]([C:35]1[N:34]([CH:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)[C:32]2[N:33]=[C:28]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([C:19]([N:18]4[CH:16]5[CH2:15][CH2:14][CH:13]4[CH2:12][NH:11][CH2:17]5)=[O:20])=[CH:22][N:23]=3)[N:29]=[CH:30][C:31]=2[CH:36]=1)=[O:41]

Participants

3

Reactant 1

HCID 67355731HCID 67355731, compound

Product 1

HCID 67356908HCID 67356908, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of the 8-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1]octane-3-carboxylic acid benzyl ester (550 mg, 0.883 mmol) and 10% Pd/C (100 mg, 0.1 eq), in methanol (10 mL) was evacuated and then purged with N2 3 times and then backfilled with hydrogen under balloon pressure and stirred for 16 hr. The reaction mixture was then filtered through a pad of Celite and the filtrate concentrated to a colorless oil. To the oil was added ethyl acetate/heptane and the resulting precipitate triturated which gave 7-cyclopentyl-2-[5-(3,8-diaza-bicyclo[3.2.1]octane-8-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as a white solid (260 mg, 0.532 mmol) in 60% yield. 1H NMR (400 MHz, MeOD) δ ppm 1.68-1.84 (m, 2H) 1.94-2.12 (m, 8H) 2.12-2.18 (m, 1H) 2.45-2.61 (m, 2H) 2.77 (br. s., 2H) 2.93-3.11 (m, 2H) 3.16 (s, 6H) 4.16 (br. s., 1H) 4.64 (br. s., 1H) 4.80 (t, J=8.84 Hz, 1H) 6.64 (s, 1H) 7.92 (dd, J=8.59, 2.53 Hz, 1H) 8.47-8.57 (m, 2H) 8.85 (s, 1H); MS m/z 489.9 (M+H)+.

Workup

  1. customin methanol (10 mL) was evacuated
  2. custompurged with N2 3 times
  3. filtrationThe reaction mixture was then filtered through a pad of Celite
  4. concentrationthe filtrate concentrated to a colorless oil
  5. additionTo the oil was added ethyl acetate/heptane
  6. customthe resulting precipitate triturated which

Sources & evidence

ORD record
ord-d865037f5de7473d8884eb9691121d0f
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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