HCID 58381236, compound → HCID 58381233, compound

HRID 1025812Notes

Reaction equation

HRID 1025812 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[N:19]=[N:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=5)=[CH:33][CH:32]=4)[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:22][CH:21]=3)=[N:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1.O>[CH3:28][C:27]([CH3:30])([CH3:29])[CH:26]([C:31]1[CH:32]=[CH:33][C:34]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)=[CH:35][CH:36]=1)[C:23]1[CH:22]=[CH:21][C:20]([C:17]2[N:18]=[N:19][N:15]([CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:16]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 1

HCID 58381236HCID 58381236, compound

Product 1

HCID 58381233HCID 58381233, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Crude 2h (0.102 mmol) was dissolved in a pre-mixed solution of 4N HCl in dioxane (5.00 mL) and deionized water (250 μL) at 10° C. The resultant solution was warmed to room temperature and aged for approximately 1.3 h. After concentrating in vacuo, the residue was purified by flash chromatography on silica gel [100% EtOAc (120 mL) followed by 0%-100% EtOAc/(DCM:MeOH:ammonium hydroxide (95:5:1)] to afford compound Ie-2bx, Ie-2bx: m/z (ES) 497 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.59 (d, 1H, J=4.3 Hz), 8.05 (d, 2H, J=8.2 Hz), 7.70 (dt, 1H, J=7.6, 1.4 Hz), 7.53 (m, 3H), 7.36 (d, 2H, J=8.7 Hz), 7.21 (dd, 1H, J=6.9, 5.1 Hz), 6.92 (d, 2H, J=8.4 Hz), 5.19 (s, 2H), 4.51 (d, 2H, J=7.1 Hz), 3.75 (s, 1H), 3.10 (bd, 2H, J=12.4 Hz), 2.60 (dt, 2H, J=12.1, 2.0 Hz), 2.21 (m, 1H), 1.86 (bs, 1H), 1.60 (bd, 2H, J=12.3 Hz), 1.28 (m, 2H), 1.04 (s, 9H).

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe residue was purified by flash chromatography on silica gel [100% EtOAc (120 mL)
  3. customto afford compound Ie-2bx

Sources & evidence

ORD record
ord-58e1649d20874ee199925d37a6cde1ab
Source dataset
uspto-grants-2014_05
Patent number
US08729104B2

Reaction notes

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