Hydrochloric Acid → HCID 71726647, compound

HRID 870944Notes

Reaction equation

HRID 870944 reaction equation
[CH3:1][CH:2]([CH3:32])[CH2:3][C@H:4]([NH:24]C(=O)OC(C)(C)C)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:23]3[C:18](=[CH:19][N:20]=[CH:21][CH:22]=3)[C:14]3([CH2:17][O:16][CH2:15]3)[O:13][C:11]=2[CH:12]=1.[ClH:33].C(OCC)C>ClCCl>[NH2:24][C@@H:4]([CH2:3][CH:2]([CH3:32])[CH3:1])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:23]3[C:18](=[CH:19][N:20]=[CH:21][CH:22]=3)[C:14]([CH2:17][OH:16])([CH2:15][Cl:33])[O:13][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86724434HCID 86724434, compound

Product 1

HCID 71726647HCID 71726647, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((S)-tert-butyl (4-methyl-1-(spiro[chromeno[3,4-c]pyridine-5,3′-oxetan]-8-yloxy)pentan-2-yl)carbamate (10 mg, 0.023 mmol) (prepared as described in Example 19, Part D) in dichloromethane (1 mL) cooled to 0° C. was added 1M HCl in diethyl ether (234, 0.023 mmol) dropwise and the solution stirred for 30 min. The reaction was then warmed to room temperature and stirred for 2 h. After completion of reaction, the volatiles were removed under reduced and purified by preparative HPLC to afford product (8-(((S)-2-amino-4-methylpentyl)oxy)-5-(chloromethyl)-5H-chromeno[3,4-c]pyridin-5-yl)methanol (2.08 mg, 5.52 μmol, 24% yield) as a yellow solid. 1H NMR (400 MHz, MeOD) δ 8.82 (m, 1H), 8.69 (m, 1H), 8.35 (m, 1H), 8.09 (m, 1H), 6.94 (m, 1H), 6.82 (s, 1H), 4.36-4.20 (m, 6H), 3.73 (m, 1H), 1.82-1.68 (m, 3H), 1.04 (m, 6H); LCMS (ESI) m/e 377.2 [(M+H)+, calcd for C20H26ClN2O3 377.2]; LC/MS retention time (Method E): tR=1.71 min; HPLC retention time (method A): tR=8.12 min; HPLC retention time (method B): tR=9.87 min.

Workup

  1. stirringstirred for 2 h
  2. customAfter completion of reaction
  3. customthe volatiles were removed
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-fb01d18f3d934aa483559451792e8f34
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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