Hydrochloric Acid → HCID 89652879, compound

HRID 1479055Notes

Reaction equation

HRID 1479055 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([N:23]1[CH2:37][C:26]2=[C:27]3[N:32]([N:33]=[C:25]2[CH2:24]1)[C:31]([CH3:34])=[C:30]([Cl:35])[C:29]([CH3:36])=[N:28]3)=[O:22])=O)(C)(C)C.Cl>C(Cl)Cl>[Cl:35][C:30]1[C:29]([CH3:36])=[N:28][C:27]2[N:32]([N:33]=[C:25]3[CH2:24][N:23]([C:21]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[O:14][CH2:13][C@H:9]4[CH2:10][CH2:11][CH2:12][NH:8]4)=[O:22])[CH2:37][C:26]3=2)[C:31]=1[CH3:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89649969HCID 89649969, compound

Product 1

HCID 89652879HCID 89652879, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-2-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (90 mg; 0.17 mmol; 1 eq.) and 2M HCl (3 mL; 6 mmol; 35 eq.) in DCM (5 mL) was stirred at room temperature for 18 hours then concentrated to dryness. 1M NaOH was added and extracted several times with DCM. The combined organics were dried over magnesium sulfate and concentrated in vacuo. Crystallization from MTBE afforded the title compound (30 mg, 41%) as a yellow solid. 1H NMR (DMSO) δ 7.46-7.39 (m, 1H), 7.31-7.27 (m, 1H), 7.13 (d, J=8.4 Hz, 1H), 7.05-7.00 (m, 1H), 4.82-4.54 (m, 2H), 3.91-3.89 (m, 2H), 3.35-3.25 (m, 1H), 2.84 (s, 1.5H), 2.80 (s, 1.5H), 2.61-2.58 (m, 5H), 1.73-1.30 (m, 4H). HPLC (max plot) 97.1%, Rt 2.65 min. UPLC/MS: (MS+) 426.2 ([M+H]+).

Workup

  1. concentrationthen concentrated to dryness
  2. addition1M NaOH was added
  3. extractionextracted several times with DCM
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customCrystallization from MTBE

Sources & evidence

ORD record
ord-c66c06bff0134b928825641722c1d880
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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