Acetic Acid → HCID 59814686, compound

HRID 1994447Notes

Reaction equation

HRID 1994447 reaction equation
BrC1C=CC2N([CH:16]3[CH2:21]CN[CH2:18][CH2:17]3)C3C(SC=2C=1)=CC=CC=3.[CH:22]12[NH:29][CH:26]([CH2:27][CH2:28]1)[CH2:25][CH:24]([N:30]1[C:43]3[CH:42]=[CH:41][C:40]([Br:44])=[CH:39][C:38]=3[S:37][C:36]3[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:23]2.[C:45](O)(=[O:47])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.CN(C=O)C>[Br:44][C:40]1[CH:41]=[CH:42][C:43]2[N:30]([CH:24]3[CH2:23][CH:22]4[N:29]([CH2:21][C:16]5[CH:17]=[CH:18][O:47][CH:45]=5)[CH:26]([CH2:27][CH2:28]4)[CH2:25]3)[C:31]3[C:36]([S:37][C:38]=2[CH:39]=1)=[CH:35][CH:34]=[CH:33][CH:32]=3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11516034HCID 11516034, compoundHCID 59814692HCID 59814692, compound

Product 1

HCID 59814686HCID 59814686, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-bromo-10-piperidin-4-yl-10H-phenothiazine, 4i (11.2 mg; 0.029 mmol) and 3-furyl carboxaldehyde (8.4 mg; 0.087 mmol) in dichloroethane (120 μL) was added acetic acid (5 μL) and a solution of sodium triacetoxyborohydride (12 mg, 0.057 mmol) in DMF (100μ). The mixture was stirred at rt for 18 h, quenched with water (50 μL), and lyophilized. The thus obtained crude 3-bromo-10-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenothiazine, 5i as a mixture of endo and exo isomers was used as such for the next reaction.

Workup

  1. customquenched with water (50 μL)

Sources & evidence

ORD record
ord-d0c0bb20ab384f0696eab7db6d0a3f2f
Source dataset
uspto-grants-2010_01
Patent number
US07652005B2

Reaction notes

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