5-Bromopyridine-2,3-diamine → HCID 59243059, compound

HRID 1644614Notes

Reaction equation

HRID 1644614 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([OH:15])[CH:14]=1)[C:9](O)=O.Br[C:21]1[CH:22]=[C:23]([NH2:28])[C:24]([NH2:27])=[N:25][CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:8]([C:9]2[NH:28][C:23]3[C:24]([N:27]=2)=[N:25][CH:26]=[CH:21][CH:22]=3)[CH:7]=1

Participants

5

Reactant 3

HCID 6911565-Bromopyridine-2,3-diamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59243016HCID 59243016, compound

Product 1

HCID 59243059HCID 59243059, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of 3-(2-fluorobenzyloxy)-5-hydroxybenzoic acid (3.9 g, 15 mmole, 1.0 eq.) with 5-bromo-2,3-diaminopyridine (5.6 g, 30 mmole, 2 eq.), HBTU (11.3 g, 30 mmole, 2 eq.) and TEA (5.2 mL) in DMF (40 mL) over 18 h gave the amide intermediate (LC/MS calculated and found (M+2H+)=434 and 416 final product). This intermediate was isolated by pouring the reaction mixture into 400 g of ice water and filtering the subsequent white solid which formed. After the solid was thoroughly dried to 6.2 g, the material was brought through to the next step. The solid (2 g) was dissolved in 10 mL of ethyl alcohol and 10 mL of glacial acetic acid and put in the microwave at 180° C. for 30 min. This was repeated two more times to bring all 6.2 g through to the final product. This product crashed out of solution and was isolated as a brown solid after cooling the mixture to 0° C. for 10 h. The light tan solid (5.6 g) had an LC/MS with a calculated and found (M+H+)=416.

Sources & evidence

ORD record
ord-4f67b3b8094a48e4b77c0414e10d890a
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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