Hydrochloric Acid → HCID 86695183, compound

HRID 1504027Notes

Reaction equation

HRID 1504027 reaction equation
[Si]([O:8][C@H:9]([CH3:43])[CH2:10][NH:11][C:12]([CH2:14][C@H:15]1[CH2:26][CH2:25][C:24]2[S:23][C:22]3[C:17](=[C:18]([O:27][CH:28]4[CH2:33][CH2:32][CH:31]([N:34](C)[C:35](=O)OC(C)(C)C)[CH2:30][CH2:29]4)[N:19]=[CH:20][N:21]=3)[C:16]1=2)=[O:13])(C(C)(C)C)(C)C.Cl>ClCCl>[OH:8][C@H:9]([CH3:43])[CH2:10][NH:11][C:12](=[O:13])[CH2:14][C@H:15]1[CH2:26][CH2:25][C:24]2[S:23][C:22]3[C:17](=[C:18]([O:27][CH:28]4[CH2:29][CH2:30][CH:31]([NH:34][CH3:35])[CH2:32][CH2:33]4)[N:19]=[CH:20][N:21]=3)[C:16]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86695184HCID 86695184, compound

Product 1

HCID 86695183HCID 86695183, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-(4-[[(3R)-3-([[(2R)-2-[(tert-butyldimethylsilyl)oxy]propyl]carbamoyl]methyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (60 mg, 0.09 mmol, 1.00 equiv) in dichloromethane (2 mL) was added hydrogen chloride (6 N) (1 mL). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was concentrated under vacuum. The crude product (50 mg) was purified by preparative HPLC under the following conditions: column: SunFire Prep C18, 19*150 mm 5 um; mobile phase: water with 50 mL NH4CO3 and CH3CN (5.0% CH3CN up to 43.0% in 12 min, up to 95.0% in 2 min, down to 5.0% in 2 min); detector: 254/220 nm. This resulted in 22 mg (55%) of N-[(2R)-2-hydroxypropyl]-2-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetamide as a white solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customThe crude product (50 mg) was purified by preparative HPLC under the following conditions
  3. waitmobile phase: water with 50 mL NH4CO3 and CH3CN (5.0% CH3CN up to 43.0% in 12 min
  4. waitup to 95.0% in 2 min
  5. waitdown to 5.0% in 2 min)
  6. customThis resulted in 22 mg (55%) of N-[(2R)-2-hydroxypropyl]-2-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetamide as a white solid

Sources & evidence

ORD record
ord-dc2f2cdeed2d4e6d94e3b7cab4e87300
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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