Hydrochloric Acid → HCID 89813723, compound

HRID 2276307Notes

Reaction equation

HRID 2276307 reaction equation
[Cl:1][C:2]1[C:3]([NH:31][C:32]2[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=2[C:34]([NH:36][CH3:37])=[O:35])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][CH:17]([N:19]4[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]4)[CH2:16][CH2:15][CH2:14][C:13]=3[C:28]=2[O:29][CH3:30])=[N:6][CH:7]=1.Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[C:3]([NH:31][C:32]2[CH:41]=[CH:40][CH:39]=[CH:38][C:33]=2[C:34]([NH:36][CH3:37])=[O:35])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][CH:17]([N:19]4[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]4)[CH2:16][CH2:15][CH2:14][C:13]=3[C:28]=2[O:29][CH3:30])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 78158242HCID 78158242, compound

Product 1

HCID 89813723HCID 89813723, compoundYield 203.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(5-Chloro-2-{6-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino}-pyrimidin-4-ylamino)-N-methyl-benzamide (4.90 g, 8.45 mmol) and 2.5 M of HCl in ethanol (13.5 mL, 33.8 mmol) were heated until they dissolved in ethanol (164 mL). The reaction was concentrated two times from ethanol, then warmed in a small amount of ethanol until completely dissolved. This solution was allowed to cool slowly with a stirring (<100 rpm). A solid precipitate formed quickly before the solution had cooled. This mixture was allowed to stir until ambient temperature was achieved and then filtered. The solid was washed with ethanol followed by ether then directly pumped dry under high vac to give 2-(5-chloro-2-{6-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino}-pyrimidin-4-ylamino)-N-methyl-benzamide hydrochloride (5.3 grams, quantitative yield). 1H-NMR (MeOD, 400 MHz) δ 8.55 (s, 1H), 8.17 (s, 1H), 7.80 (d, J=7.7 Hz, 1H), 7.55 (t, J=6.8 Hz, 1H), 7.46 (broad s, 1H), 7.36 (t, J=7.2 Hz, 1H), 7.23 (d, J=8.5 Hz, 1H), 4.00-3.95 (m, 4H), 3.83-3.72 (m, 5H), 3.73 (s, 3H), 3.65-3.59 (m, 2H), 3.47-3.38 (m, 5H), 2.95 (s, 3H), 2.72-2.65 (m, 1H), 2.44-2.38 (m, 1H), 2.29-2.28 (m, 1H), 2.19-2.12 (m, 1H), 1.59-1.49 (m, 1H). LC/MS (ESI+) m/z=580 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated two times from ethanol
  2. temperaturewarmed in a small amount of ethanol
  3. dissolutionuntil completely dissolved
  4. temperatureto cool slowly with a stirring (<100 rpm)
  5. customA solid precipitate formed quickly before the solution
  6. temperaturehad cooled
  7. filtrationfiltered
  8. washThe solid was washed with ethanol
  9. customthen directly pumped dry under high vac

Sources & evidence

ORD record
ord-c9fbd88436af43c6a4b2fee965687531
Source dataset
uspto-grants-2015_09
Patent number
US09132128B2

Reaction notes

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