Hydrochloric Acid → HCID 86695101, compound

HRID 1503926Notes

Reaction equation

HRID 1503926 reaction equation
[OH:1][CH:2]([CH3:31])[CH2:3][C@H:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([NH:16][CH:17]4[CH2:22][CH2:21][CH:20]([NH:23]C(=O)OC(C)(C)C)[CH2:19][CH2:18]4)[C:6]=3[C:5]1=2.Cl>ClCCl>[NH2:23][CH:20]1[CH2:21][CH2:22][CH:17]([NH:16][C:7]2[C:6]3[C:5]4[C@@H:4]([CH2:3][CH:2]([OH:1])[CH3:31])[CH2:15][CH2:14][C:13]=4[S:12][C:11]=3[N:10]=[CH:9][N:8]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68115512HCID 68115512, compound

Product 1

HCID 86695101HCID 86695101, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask containing tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino]cyclohexyl)carbamate (109 mg, 0.24 mmol, 1.00 equiv) in dichloromethane (10 mL) at 0° C. Then hydrochloric acid (12 M, 2.0 mL) was added and the resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 8 with saturated aqueous sodium carbonate and extracted with 2×40 mL of ethyl acetate. The organic layers were combined and dried over sodium sulfate and concentrated under vacuum to give the desired 1-[(3R)-12-[(4-amino cyclohexyl)amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol (70 mg, crude) as a colorless oil.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. extractionextracted with 2×40 mL of ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3155db92390e4e16a5a6b9fd115b25b0
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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