2-Amino-4-bromopyridine → HCID 58109122, compound

HRID 1046185Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.[NH2:35][C:36]1[CH:41]=[C:40](Br)[CH:39]=[CH:38][N:37]=1>>[NH2:35][C:36]1[CH:41]=[C:40]([C:17]2[CH:18]=[CH:19][C:14]([C@@H:12]([N:8]3[CH2:7][CH2:6][C@:5]([CH2:4][CH2:3][CH2:2][OH:1])([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[O:10][C:9]3=[O:11])[CH3:13])=[CH:15][CH:16]=2)[CH:39]=[CH:38][N:37]=1

Participants

Reactant 2

HCID 6932822-Amino-4-bromopyridine

HCID 59635633(R)-6-(3-hydroxypropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 58109122HCID 58109122, compound

Procedure

The title compound was prepared from (R)-6-(3-hydroxypropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one and 2-amino-4-bromopyridine following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=0.951, m/z=432; 1H NMR (CDCl3) 1.26-1.40 (m, 1H), 1.48 (d, 3H), 1.59-1.63 (m, 1H), 1.83-1.95 (m, 2H), 2.09-2.20 (m, 1H), 2.21-2.37 (m, 2H), 2.86 (m, 1H), 3.50 (m, 2H), 4.54-4.75 (s, 2H), 5.62 (m, 1H), 6.56 (s, 1H), 6.71 (d, 1H), 6.90 (d, 2H), 7.21-7.33 (m, 7H), 8.00 (m, 1H).

Sources & evidence

ORD record: ord-f08f7b58fb664e22997fd0b961169c6f
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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