Hydrochloric Acid → (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6-(piperidin-4-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626643Notes

Reaction equation

HRID 1626643 reaction equation
[CH:1]1([NH:4][C:5](=[O:43])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][C@@H:37]4[CH3:42])[C:16]4[CH2:21][N:20]([CH2:22][CH:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)[CH2:19][C:17]=4[N:18]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.CO>O1CCOCC1>[CH:1]1([NH:4][C:5]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]=[C:15]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][C@@H:37]4[CH3:42])[C:16]4[CH2:21][N:20]([CH2:22][CH:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]5)[CH2:19][C:17]=4[N:18]=3)=[CH:11][CH:12]=2)=[O:43])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66679044(S)-tert-butyl 4-((2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 66679207(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6-(piperidin-4-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)ureaYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-butyl 4-((2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)methyl)piperidine-1-carboxylate (example 128) (24 mg, 0.04 mmol) was stirred in a solution of 4M HCl in dioxane (1 mL), and methanol (0.5 mL) until analysis by LCMS indicated reaction was complete. Reaction mixture was then purified by TsOH cartridge (loaded in MeOH eluted with 2M methanolic ammonia) to afford an orange brown solid (4.9 mg, 0.009 mmol, 25%).

Workup

  1. customreaction
  2. customReaction mixture
  3. customwas then purified by TsOH cartridge (loaded in MeOH eluted with 2M methanolic ammonia)

Sources & evidence

ORD record
ord-c7a6594699b2403787cddc3d11df0a94
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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