Hydrazine hydrate (1:1) → 2-{[(4-Amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-nicotinic acid

HRID 251057

반응식

HRID 251057 반응식
[CH3:1][C:2]1[C:3]([CH2:9][NH:10][CH2:11][C:12]2[C:17](N3CCOCC3)=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.O=C1C2C(=CC=CC=2)C(=O)[N:26]1[CH2:35][CH2:36][CH2:37][CH:38]=O.[BH-](OC(C)=O)(OC(C)=O)[O:41][C:42](C)=[O:43].[Na+].NN.O>>[NH2:26][CH2:35][CH2:36][CH2:37][CH2:38][N:10]([CH2:11][C:12]1[N:13]=[CH:14][CH:15]=[CH:16][C:17]=1[C:42]([OH:43])=[O:41])[CH2:9][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=1

참가 물질

5

반응물 4

HCID 24654Hydrazine hydrate (1:1)HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 5049666Sodium triacetoxyborohydrideHCID 67272702(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-morpholin-4-yl-pyridin-2-ylmethyl)-amine

생성물 1

HCID 589972112-{[(4-Amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-nicotinic acid

실험 절차

Using General Procedure B: Reaction of C-(3-morpholin-4-yl-pyridin-2-yl)-methylamine, 3.5-dimethyl-pyridine-2-carbaldehyde and NaBH(OAc)3 gave (3,5-dimethyl-pyridin-2-ylmethyl)-(3-morpholin-4-yl-pyridin-2-ylmethyl)-amine as a colorless oil. 1H NMR (CDCl3) δ 2.27 (s, 3H), 2.30 (s, 3H), 2.92-2.95 (m, 4H), 3.79-3.82 (m, 4H), 3.95 (s, 2H), 4.03 (s, 2H), 7.14 (dd, 1H, J=4.5, 8.1 Hz), 7.23 (s, 1H), 7.33 (dd, 1H, J=1.2, 8.1 Hz), 8.22 (s, 1H), 8.31 (dd, 1H, J=1.2, 4.5 Hz). Further reaction of (3,5-dimethyl-pyridin-2-ylmethyl)-(3-morpholin-4-yl-pyridin-2-ylmethyl)-amine, 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde and NaBH(OAc)3 following General Procedure B gave a colorless oil. Deprotection with NH2NH2.H2O, following General Procedure E, gave a colorless oil. Subsequent conversion to the HBr salt gave COMPOUND 201 as a pale yellow solid. 1H NMR (D2O) δ 1.58-1.70 (m, 4H), 2.42 (s, 3H), 2.44 (s, 3H), 2.78-2.84 (m, 2H), 2.94-3.02 (m, 2H), 3.04 (s, br., 4H), 3.96 (s, br., 4H), 4.24 (s, 2H), 4.28 (s, 2H), 7.80-7.88 (m, 1H), 8.07-8.15 (m, 2H), 8.8.36-8.42 (m, 2H); 13C NMR (D2O) δ 17.21, 17.49, 23.06, 25.05, 39.66, 51.91, 52.65, 54.34, 55.96, 66.81, 126.80, 135.15, 136.40, 137.34, 137.78, 137.91, 147.61, 148.92, 149.75. ES-MS m/z 384 (M+H). Anal. Calcd. for C22H33N5O.3.3HBr.1.5H2O.0.3C4H10O: C, 39.82; H, 6.09; N, 10.01; Br, 37.68. Found: C, 39.83; H, 6.20; N, 10.08; Br, 37.59.

후처리

  1. customgave a colorless oil
  2. customgave a colorless oil

출처 및 근거

ORD 기록
ord-d92d36e717ce49979de87db12ddfd345
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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