Acetic Acid → HCID 178505712, compound

HRID 2415615Notes

Reaction equation

HRID 2415615 reaction equation
[F:1]C1C=CC(CO)=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)O[C:21](=O)[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2)=O.[Cl:32][C:33]1[CH:42]=[C:41]2[C:36]([C:37]([NH:43][CH:44]3[CH2:49][CH2:48][CH:47]([NH2:50])[CH2:46][CH2:45]3)=[CH:38][CH:39]=[N:40]2)=[CH:35][CH:34]=1.C(O)(=O)C.C([BH3-])#N>ClCCl>[Cl:32][C:33]1[CH:42]=[C:41]2[C:36]([C:37]([NH:43][C@H:44]3[CH2:45][CH2:46][C@@H:47]([NH:50][CH2:21][C:20]4[CH:15]=[CH:16][CH:17]=[C:18]([F:1])[CH:19]=4)[CH2:48][CH2:49]3)=[CH:38][CH:39]=[N:40]2)=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 680224-Fluorobenzylic alcoholHCID 159087TriacetoxyperiodinaneHCID 498716Cyano-borohydrideHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine

Product 1

HCID 178505712HCID 178505712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-fluorobenzyl alcohol (9.2 mg, 0.073 mmol) was added Dess-Martin periodinane (31.0 mg, 0.073 mmol) in dichloromethane (2 mL). The mixture was stirred at room temperature for 0.5 hour and was added to a mixture of N-(7-chloroquinolin-4-yl)-cyclohexane-1,4-diamine (20 mg, 0.073 mmol), acetic acid (0.008 mg, 0.13 mmol) and MP-cyanoborohydride (51 mg, 0.219 mmol, Argonaut Technologies) in dichloromethane (5 mL). The mixture was stirred at room temperature for 18 hours, filtered and concentrated under reduced pressure to provide the τιτλεδ compound. MS(ESI) m/e 384 (M+H)+; 1H NMR (500 MHz, DMSO-D6) δ ppm 8.91 (br.s, 2 H), 8.75 (d, 1 H), 8.61 (d, 1 H), 7.97 (d, 1 H), 7.81 (dd, 1 H), 7.52 (dd, 1 H), 7.42 (d, 1 H), 7.37 (d, 1 H), 7.29 (td, 1 H), 4.25 (br.s, 2 H), 4.09 (br.s, 2 H), 1.76-2.13 (m, 8 H).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customto provide the τιτλεδ compound

Sources & evidence

ORD record
ord-f36bd8de86c74affacf0bcca32ea8290
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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