Trifluoroacetic acid → HCID 58997186, compound

HRID 251071Notes

Reaction equation

HRID 251071 reaction equation
C(OC(=O)[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:8])(C)(C)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:33]2[C:34]([CH:39]=O)=[N:35][CH:36]=[CH:37][CH:38]=2)([CH3:32])[CH3:31])=[CH:26][CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(C(F)(F)F)=O.NCCCCN(CC1N=CC=CC=1C(O)=O)CC1C(C)=CC(C)=CN=1>>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([C:33]2[C:34]([CH2:39][N:13]([CH2:14][C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:12][CH2:11][CH2:10][CH2:9][NH:7][CH3:8])=[N:35][CH:36]=[CH:37][CH:38]=2)([CH3:32])[CH3:31])=[CH:28][CH:29]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 589972112-{[(4-Amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-nicotinic acidHCID 67271861{4-[(3-Fluoro-pyridin-2-ylmethyl)-amino]-butyl}-methyl-carbamic acid tert-butyl esterHCID 865947683-[1-(4-Chloro-phenyl)-1-methyl-ethyl]-pyridine-2-carbaldehyde

Product 1

HCID 58997186HCID 58997186, compound

Procedure

Using General Procedure B, {4-[(3-fluoro-pyridin-2-ylmethyl)-amino]-butyl}-methyl-carbamic acid tert-butyl ester, 3-[1-(4-chloro-phenyl)-1-methyl-ethyl]-pyridine-2-carbaldehyde and NaBH(OAc)3 were reacted to give a pale yellow oil. Deprotection with TFA using General Procedure F and conversion to the HBr salt using General Procedure D gave a white solid. 1H NMR (D2O) δ 1.21-1.25 (m, 2H), 1.36-1.42 (m, 2H), 1.67 (s, 6H), 2.30-2.36 (m, 2H), 2.65 (s, 3H), 2.89-2.91 (m, 2H), 3.75 (s, 2H), 4.10 (s, 2H), 7.18 (d, 2H, J=8.4 Hz), 7.32 (d, 2H, J=8.4 Hz), 7.87-7.94 (m, 1H), 8.19 (t, 1H, J=8.7 Hz), 8.58 (d, 1H, J=5.1 Hz), 8.66 (dd, 1H, J=5.7, 8.7 Hz); 13C NMR (D2O) δ 21.64, 23.34, 29.58, 33.16, 42.64, 48.88, 50.52, 53.30, 54.88, 126.15, 128.30 (d, J=7 Hz), 128.50, 129.41, 131.78 (d, J=19 Hz), 132.40, 140.91, 141.13, 141.21, 141.33, 143.16, 146.54 (d, J=4 Hz), 150.78, 158.93 (d, J=256 Hz). ES-MS m/z 455 (M+H).

Workup

  1. customwere reacted
  2. customto give a pale yellow oil
  3. customgave a white solid

Sources & evidence

ORD record
ord-6a613c90d1db4689b11829cf9d5e614d
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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