Hydrochloric Acid → HCID 89662744, compound

HRID 1479088Notes

Reaction equation

HRID 1479088 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([N:23]2[CH2:37][C:26]3=[C:27]4[N:32]([N:33]=[C:25]3[CH2:24]2)[C:31]([CH3:34])=[C:30]([Cl:35])[C:29]([CH3:36])=[N:28]4)=[O:22])[CH2:9]1)(C)(C)C.Cl.O1CCOCC1>O>[NH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([N:23]2[CH2:37][C:26]3=[C:27]4[N:32]([N:33]=[C:25]3[CH2:24]2)[C:31]([CH3:34])=[C:30]([Cl:35])[C:29]([CH3:36])=[N:28]4)=[O:22])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131736556HCID 131736556, compound

Product 1

HCID 89662744HCID 89662744, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

{1-[2-(6-Chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-benzyl]-piperidin-3-yl}-carbamic acid tert-butyl ester (160 mg, 0.30 mmol) was added into a 4N solution of HCl in dioxane (2 mL, 8 mmol), followed by water (0.5 mL). The resulting mixture was stirred at RT for 2 hours, then concentrated under vacuum. The residue was taken up with water (5 mL) and a 1N aqueous solution of NaOH (15 mL), then extracted with DCM (2×25 mL). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum. After purification by crystallization from ACN, the title compound was obtained as a white powder (46 mg, 35%). 1H NMR (DMSO-d6) δ 7.47-7.31 (m, 4H), 4.83 (s, 1H), 4.81 (s, 1H), 4.52 (s, 1H), 4.47 (s, 1H), 3.42 (br s, 2H), 2.85 (s, 1.5H), 2.80 (s, 1.5H), 2.70-2.43 (m, 5H), 2.23-2.09 (m, 1H), 1.88-1.74 (m, 1H), 1.65-1.52 (m, 1H), 1.46-1.31 (m, 2H), 1.25 (s, 2H), 1.02-0.83 (m, 1H), 0.83-0.65 (m, 1H). HPLC (max plot) 99.4%, Rt 2.21 min. UPLC/MS: (MS+) 439.3 ([M+H]+). Melting point: 165-170° C. (ACN).

Workup

  1. concentrationconcentrated under vacuum
  2. extractiona 1N aqueous solution of NaOH (15 mL), then extracted with DCM (2×25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customAfter purification
  6. customby crystallization from ACN

Sources & evidence

ORD record
ord-28c6020eddfb42b481a151e76cdf270c
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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