Dichloromethane → Hydrochloric Acid

HRID 251113Notes

Reaction equation

HRID 251113 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.[O:25]([CH2:33][C:34]1[C:35]([CH:40]=O)=[N:36][CH:37]=[CH:38][CH:39]=1)[Si](C(C)(C)C)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)[Cl:57]>>[ClH:57].[CH3:22][C:21]1[C:16]([CH2:15][N:14]([CH2:40][C:35]2[C:34]([CH2:33][OH:25])=[CH:39][CH:38]=[CH:37][N:36]=2)[C@H:11]2[CH2:10][CH2:9][C@H:8]([NH2:7])[CH2:13][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 873329733-(Tert-butyl-dimethylsiloxymethyl)-pyridine-2-carbaldehydeHCID 178430558HCID 178430558, compound

Product 2

HCID 313Hydrochloric AcidHCID 178430550HCID 178430550, compound

Procedure

Using General Procedure B: Reaction of {trans-4-[(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester and 3-(tert-butyl-dimethylsiloxymethyl)-pyridine-2-carbaldehyde in CH2Cl2 (4 mL) with NaBH(OAc)3 gave the crude material. Deprotection with 6 N HCl gave the amine as a white foamy solid. Conversion to the HBr salt using General Procedure D gave COMPOUND 257 as a white solid. 1H NMR (D2O) δ 1.33-1.62 (m, 4H), 2.06-2.13 (m, 4H), 2.40 (s, 3H), 2.41 (s, 3H), 2.74 (t br, 1H, J=11.4 Hz), 3.14 (t br, 1H, J=11.4 Hz), 4.20 (s, 2H), 4.35 (s, 2H), 4.84 (s, 2H), 7.89 (dd, 1H, J=7.8, 5.1 Hz), 8.10 (s, 1H), 8.32 (s, 1H), 8.48 (d, 1H, J=7.8 Hz), 8.61 (d, 1H, J=5.1 Hz). 13C NMR (D2O) δ 17.05, 17.44, 25.86 (2), 29.48 (2), 49.67, 50.68, 51.02, 59.43, 60.73, 126.55, 136.72, 137.44, 138.30, 139.13, 140.83, 145.85, 148.11, 148.86, 151.63. ES-MS m/z 355 (M+H). Anal. Calcd. for C21H30N4O.2.9HBr.1.8H2O: C, 40.58; H, 5.92; N, 9.01; Br, 37.28. Found: C, 40.28; H, 6.04; N, 8.79; Br, 37.52.

Workup

  1. customgave the crude material

Sources & evidence

ORD record
ord-bc41c047aef04d45bac50c9213173e29
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…