Hydrochloric Acid → HCID 118436351, compound

HRID 1775478Notes

Reaction equation

HRID 1775478 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:40])([CH3:39])[C:9]([N:11]1[CH2:15][CH2:14][C@@:13]([N:17]2[C:21]3[N:22]=[C:23]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[N:24]=[C:25]([C:26]4[CH:27]=[N:28][C:29]([NH2:32])=[N:30][CH:31]=4)[C:20]=3[CH2:19][CH2:18]2)([CH3:16])[CH2:12]1)=[O:10])(C)(C)C.Cl>C1(C)C=CC=CC=1>[NH2:7][C:8]([CH3:40])([CH3:39])[C:9]([N:11]1[CH2:15][CH2:14][C@@:13]([N:17]2[C:21]3[N:22]=[C:23]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[N:24]=[C:25]([C:26]4[CH:31]=[N:30][C:29]([NH2:32])=[N:28][CH:27]=4)[C:20]=3[CH2:19][CH2:18]2)([CH3:16])[CH2:12]1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118447873HCID 118447873, compound

Product 1

HCID 118436351HCID 118436351, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a foil covered flask, a solution of tert-butyl(1-{(3S)-3-[4-(2-aminopyrimidin-5-yl)-2-(morpholin-4-yl)-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-3-methylpyrrolidin-1-yl}-2-methyl-1-oxopropan-2-yl)carbamate (369 mg, 0.65 mmol) in MeON (3 mL) was treated with HCl (3 mL, 4N in dioxane) and the mixture was stirred at room temperature for 18 h. The mixture was diluted with toluene and concentrated. The residue was dissolved in a minimum amount of MeOH, dropped into aqueous NaHCO3 and extracted with 15% i-PrOH in DCM (4×). The extracts were washed with brine, dried over MgSO4 and concentrated. The oily residue was suspended in a few mL of acetonitrile and sonicated briefly, inducing crystallization. The resulting solids were collected by filtration to give the title compound (206 mg, 68%) as an off-white solid. 1H NMR (400 MHz, 80° C., DMSO-d6) δ 8.73 (s, 2 H), 6.68 (br s, 2 H), 4.40-4.00 (m, 2 H), 3.73-3.50 (m, 12 H), 3.12-3.07 (m, 2H, partially overlapped with water), 2.41-2.30 (m, 1 H), 2.06-1.97 (m, 1 H), 1.74 (br s, 2 H), 1.31 (s, 3 H), 1.27 (s, 6 H). m/z (APCI+) for C23H33CN9O2 468.3 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in a minimum amount of MeOH
  3. additiondropped into aqueous NaHCO3
  4. extractionextracted with 15% i-PrOH in DCM (4×)
  5. washThe extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customsonicated briefly
  9. customcrystallization
  10. filtrationThe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-22ac4fe621fd400ea00884a7ce7c7839
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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