4-Pyridinecarboxaldehyde → (S)-(3-chloro-5-trifluoromethyl-benzyl)-(7,9-dimethyl-1-pyridin-4-ylmethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)-amine

HRID 507182Notes

Reaction equation

HRID 507182 reaction equation
FC1C=C(C=C(C(F)(F)F)C=1)CN([C@H]1CCCN([CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)C2C=C(C(F)(F)F)C(C)=CC1=2)C1N=NN(C)N=1.[Cl:43][C:44]1[CH:45]=[C:46]([CH:72]=[C:73]([C:75]([F:78])([F:77])[F:76])[CH:74]=1)[CH2:47][N:48]([C@H:55]1[CH2:61][CH2:60][CH2:59][NH:58][C:57]2[C:62]([CH3:71])=[C:63]([C:67]([F:70])([F:69])[F:68])[C:64]([CH3:66])=[CH:65][C:56]1=2)[C:49]1[N:50]=[N:51][N:52]([CH3:54])[N:53]=1.N1C=CC(C=O)=CC=1>ClC(Cl)C>[Cl:43][C:44]1[CH:45]=[C:46]([CH:72]=[C:73]([C:75]([F:78])([F:76])[F:77])[CH:74]=1)[CH2:47][N:48]([C@H:55]1[CH2:61][CH2:60][CH2:59][N:58]([CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[C:57]2[C:62]([CH3:71])=[C:63]([C:67]([F:68])([F:69])[F:70])[C:64]([CH3:66])=[CH:65][C:56]1=2)[C:49]1[N:50]=[N:51][N:52]([CH3:54])[N:53]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 59432360(S)-(3-fluoro-5-trifluoromethyl-benzyl)-(7-methyl-1-pyridin-4-ylmethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)-amineHCID 59432530(S)-(3-chloro-5-trifluoromethyl-benzyl)-(7,9-dimethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)-amine

Product 1

HCID 59432309(S)-(3-chloro-5-trifluoromethyl-benzyl)-(7,9-dimethyl-1-pyridin-4-ylmethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)-amine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Prepare the title compound by essentially following the procedure described in the synthesis of (S)-(3-fluoro-5-trifluoromethyl-benzyl)-(7-methyl-1-pyridin-4-ylmethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)-amine (Example 186, Step 2) by using (S)-(3-chloro-5-trifluoromethyl-benzyl)-(7,9-dimethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)-amine (0.08 g, 0.15 mmol) and pyridine-4-carboxaldehyde (0.045 mL, 0.45 mmol) in dichloroethane (2 mL) at room temperature for 15 h to afford the title compound. Purification by silica gel column (gradient eluent, 0-5% MeOH in ethyl acetate) provides the title compound (0.09 g, 91%). MS (ES+): 624 (M+H).

Workup

  1. customat room temperature
  2. customfor 15 h

Sources & evidence

ORD record
ord-7cadf6c0f4734125b47ce36d98f67ba6
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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