Dimethylformamide → HCID 24772748, compound

HRID 1272697Notes

Reaction equation

[C:1]([C:5]1[CH:43]=[CH:42][C:8]([O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([C:26]([NH:28][C@H:29]([CH2:33][C:34]4[S:35][C:36]([CH:39]([CH3:41])[CH3:40])=[CH:37][CH:38]=4)[C:30]([OH:32])=O)=[O:27])[N:16]=[C:17]3[CH2:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=N[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][C:53]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:70](C(C)C)C(C)C.CN([CH:80]=[O:81])C>>[CH2:80]([O:81][NH:70][C:30]([CH:29]([NH:28][C:26]([C:15]1[N:16]=[C:17]([CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[C:18]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:43][CH:42]=1)[CH:19]=2)=[O:27])[CH2:33][C:34]1[S:35][C:36]([CH:39]([CH3:41])[CH3:40])=[CH:37][CH:38]=1)=[O:32])[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 11956564HCID 11956564, compound

Product 1

HCID 24772748HCID 24772748, compound

Procedure

A solution of Example 43 (0.090 g, 0.150 mmol) in DMF was treated with o-Benzylhyroxylamine hydrochloride (27 mg, 0.165 mmol), HBTU (0.063 g, 0.165 mmol), and DIEA (0.150 mL, 0.829 mmol) by the general procedure A. The crude product was purified by flash chromatography (silica, Hexanes:EtOAc) to afford 74 mg of title compound.

Workup

customThe crude product was purified by flash chromatography (silica, Hexanes:EtOAc)

Sources & evidence

ORD record: ord-678bff5f008f41b0b3f2fa6dddec1d0c
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208601B2

Reaction notes

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